1.1
Reagents:
(Trifluoromethyl)benzene
Catalysts:
Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi…
;
3 h, -40 °C
2.1
Solvents:
Tetrahydrofuran
;
1 h, -20 °C
2.2
Reagents:
Ammonium chloride
Solvents:
Water
3.1
Reagents:
1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
,
Thionyl chloride
;
0 °C; 0.5 h, rt
3.2
Reagents:
Sodium
Solvents:
Diethyl ether
;
12 h, reflux
4.1
Reagents:
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Solvents:
Dichloromethane
,
Water
;
2 h, rt
5.1
Reagents:
Dess-Martin periodinane
Solvents:
Dichloromethane
;
1 h, rt
6.1
Catalysts:
Camphorsulfonic acid
Solvents:
Methanol
;
1 h, rt
6.2
Reagents:
Sodium bicarbonate
;
10 min, rt
7.1
Reagents:
Dess-Martin periodinane
Solvents:
Dichloromethane
;
1 h, rt
8.1
Reagents:
Butyllithium
Solvents:
Tetrahydrofuran
,
Hexane
;
30 min, 0 °C
8.2
Solvents:
Tetrahydrofuran
;
5 h, 0 °C → rt
8.3
Reagents:
Ammonium chloride
Solvents:
Water
9.1
Reagents:
Acetic acid
Solvents:
Water
;
0.5 h, 60 °C; 60 °C → rt
9.2
Reagents:
Sodium bicarbonate
Solvents:
Water
;
pH 7
9.3
Reagents:
Dess-Martin periodinane
Solvents:
Dichloromethane
;
1 h, rt
9.4
Reagents:
Hydrochloric acid
Solvents:
Tetrahydrofuran
,
Water
;
7 h, rt
Find chemicals on chem960.com, Welcome!
- chem960
- 82508-37-0
82508-37-0
（name: Deacetylpseudolaric-acid-A）
Related Compounds
- Pseudolaric Acid A；2,4-Pentadienoic acid, 5-(4a-(acetyloxy)-3,4,4a,5,6,9-hexahydro-3,7-dimethyl-1-oxo-1H-4,9a-ethanocyclohepta(c)pyran-3-yl)-2-methyl-(3alpha(2E,4E),4alpha,4aalpha,9aalpha)-(-)- | 82508-32-5
- Pseudolaric Acid C | 82601-41-0
- Methylpseudolarate B | 82508-34-7
- Methyl pseudolarate A | 82508-33-6
- Demethoxydeacetoxypseudolaric-acid-B | 82508-36-9
- Deacetylpseudolaric-acid-A
- (2E, 4E)-5-[(3R, 4R, 4αS, 9αR)-4α-Hydroxy-3, 7-dimethyl-1-oxo-3, 4, 4α, 5, 6, 9-hexahydro-4, 9α-ethanocyclohepta[c]pyran-3(1H)-yl]-2-methylpenta-2, 4-dienoic acid
- Deacetylpseudolaric acid A
- (2E,4E)-5-[(1R,7S,8R,9R)-7-Hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.0<sup>1,7</sup>]tridec-3-en-9-yl]-2-methyl-2,4-pentadienoic acid
- (-)-Deacetylpseudolaric acid A
- [ "" ]
- (2E,4E)-5-[(3R,4R,4aS,9aR)-3,4,4a,5,6,9-Hexahydro-4a-hydroxy-3,7-dimethyl-1-oxo-1H-4,9a-ethanocyclohepta[c]pyran-3-yl]-2-methyl-2,4-pentadienoic acid (ACI)
- 1H-4,9a-Ethanocyclohepta[c]pyran, 2,4-pentadienoic acid deriv. (ZCI)
- 2,4-Pentadienoic acid, 5-(3,4,4a,5,6,9-hexahydro-4a-hydroxy-3,7-dimethyl-1-oxo-1H-4,9a-ethanocyclohepta[c]pyran-3-yl)-2-methyl-, [3α(2E,4E),4α,4aα,9aα]- (ZCI)
- DTXSID401311131
- HY-N3696
- FS-9074
- CS-0024077
- CHEMBL222903
- AKOS040760364
- 1H-4,9a-Ethanocyclohepta[c]pyran, 2,4-pentadienoic acid deriv.
- (-)-Deacetylpseudolaric acid A
- 82508-37-0
- deacetylpseudolaric acid A
- (2E,4E)-5-[(1R,7S,8R,9R)-7-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo[6.3.2.01,7]tridec-3-en-9-yl]-2-methylpenta-2,4-dienoic acid
- DA-62732
- DA-62732
- DA-62732
- 11S-Deacetylpseudolarate a
- 11S-Deacetylpseudolarate a
- 11S-Deacetylpseudolarate a
- (2E,4E)-5-((1R,7S,8R,9R)-7-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo(6.3.2.01,7)tridec-3-en-9-yl)-2-methylpenta-2,4-dienoic acid
- (2E,4E)-5-((1R,7S,8R,9R)-7-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo(6.3.2.01,7)tridec-3-en-9-yl)-2-methylpenta-2,4-dienoic acid
- (2E,4E)-5-((1R,7S,8R,9R)-7-hydroxy-4,9-dimethyl-11-oxo-10-oxatricyclo(6.3.2.01,7)tridec-3-en-9-yl)-2-methylpenta-2,4-dienoic acid
- InChIKey：MQOMHFMKUJFDBH-SWRVIOJRSA-N
- Inchi：1S/C20H26O5/c1-13-6-10-19-11-8-15(20(19,24)12-7-13)18(3,25-17(19)23)9-4-5-14(2)16(21)22/h4-6,9,15,24H,7-8,10-12H2,1-3H3,(H,21,22)/b9-4+,14-5+/t15-,18+,19+,20-/m0/s1
- SMILES：O[C@]12CCC(C)=CC[C@@]31CC[C@H]2[C@@](C)(/C=C/C=C(\C)/C(=O)O)OC3=O
Computed Properties
- Exact Mass: 346.178
- Hydrogen Bond Donor Count: 2
- Hydrogen Bond Acceptor Count: 5
- Rotatable Bond Count: 3
- Monoisotopic Mass: 346.178
- Heavy Atom Count: 25
- Complexity: 703
- Isotope Atom Count: 0
- Defined Atom Stereocenter Count: 4
- Undefined Atom Stereocenter Count : 0
- Defined Bond Stereocenter Count: 2
- Undefined Bond Stereocenter Count: 0
- Covalently-Bonded Unit Count: 1
- XLogP3: 2.1
- Topological Polar Surface Area: 83.8A^2
Experimental Properties
- LogP: 3.14670
- PSA: 83.83000
- Boiling Point: 569.4±50.0 °C at 760 mmHg
- Vapor Pressure: 0.0±3.5 mmHg at 25°C
- Flash Point: 202.3±23.6 °C
- Color/Form: Powder
- Density: 1.2±0.1 g/cm3
- Safety Instruction：H303+H313+H333
- Hazard Statement：H303 may be harmful by ingestion +h313 may be harmful by skin contact +h333 may be harmful by inhalation
- Warning Statement：P264+P280+P305+P351+P338+P337+P313
- Storage Condition：Store at 4 ℃, better at -4 ℃
Synthetic Circuit 1
Reaction Conditions + Expand
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 2
Reaction Conditions + Expand
1.1
Reagents:
Dess-Martin periodinane
Solvents:
Dichloromethane
;
1 h, rt
2.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
2.2 Reagents: Sodium bicarbonate ; 10 min, rt
3.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
4.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
4.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
4.3 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
5.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
5.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
5.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
2.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
2.2 Reagents: Sodium bicarbonate ; 10 min, rt
3.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
4.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
4.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
4.3 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
5.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
5.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
5.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 3
Reaction Conditions + Expand
1.1
Reagents:
Acetic acid
Solvents:
Water
;
0.5 h, 60 °C; 60 °C → rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
1.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
1.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
1.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
1.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
1.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 4
Reaction Conditions + Expand
1.1
Reagents:
2-Methyl-2-butene
,
Monosodium phosphate
,
Sodium chlorite
Solvents:
tert-Butanol
,
Water
;
rt; 2 h, rt
2.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
2.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
3.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
4.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
4.2 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
5.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
6.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
7.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
8.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
8.2 Reagents: Sodium bicarbonate ; 10 min, rt
9.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
10.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
10.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
10.3 Reagents: Ammonium chloride Solvents: Water
11.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
11.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
11.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
11.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
2.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
2.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
3.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
4.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
4.2 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
5.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
6.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
7.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
8.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
8.2 Reagents: Sodium bicarbonate ; 10 min, rt
9.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
10.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
10.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
10.3 Reagents: Ammonium chloride Solvents: Water
11.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
11.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
11.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
11.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 5
Reaction Conditions + Expand
1.1
Solvents:
Tetrahydrofuran
;
1 h, -20 °C
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
2.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
3.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
4.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
5.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
5.2 Reagents: Sodium bicarbonate ; 10 min, rt
6.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
7.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
7.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
7.3 Reagents: Ammonium chloride Solvents: Water
8.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
8.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
8.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
8.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
2.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
3.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
4.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
5.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
5.2 Reagents: Sodium bicarbonate ; 10 min, rt
6.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
7.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
7.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
7.3 Reagents: Ammonium chloride Solvents: Water
8.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
8.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
8.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
8.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 6
Reaction Conditions + Expand
1.1
Solvents:
Tetrahydrofuran
;
0 °C; 1 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
2.2 Solvents: Dichloromethane ; 30 min, -78 °C
2.3 Reagents: Triethylamine ; 10 min, -78 °C
2.4 Reagents: Water
3.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
4.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
4.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
5.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
6.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
6.2 Reagents: Ammonium chloride Solvents: Water
7.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
7.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
8.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
9.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
10.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
10.2 Reagents: Sodium bicarbonate ; 10 min, rt
11.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
12.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
12.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
12.3 Reagents: Ammonium chloride Solvents: Water
13.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
13.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
13.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
13.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
1.2 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
2.2 Solvents: Dichloromethane ; 30 min, -78 °C
2.3 Reagents: Triethylamine ; 10 min, -78 °C
2.4 Reagents: Water
3.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
4.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
4.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
5.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
6.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
6.2 Reagents: Ammonium chloride Solvents: Water
7.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
7.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
8.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
9.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
10.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
10.2 Reagents: Sodium bicarbonate ; 10 min, rt
11.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
12.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
12.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
12.3 Reagents: Ammonium chloride Solvents: Water
13.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
13.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
13.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
13.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 7
Reaction Conditions + Expand
1.1
Reagents:
Triethylamine
,
Isobutyl chloroformate
Solvents:
Diethyl ether
,
Tetrahydrofuran
;
30 min, -20 °C; -20 °C → 0 °C
1.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
2.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
3.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
3.2 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
4.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
5.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
6.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
7.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
7.2 Reagents: Sodium bicarbonate ; 10 min, rt
8.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
9.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
9.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
9.3 Reagents: Ammonium chloride Solvents: Water
10.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
10.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
10.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
10.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
1.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
2.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
3.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
3.2 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
4.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
5.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
6.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
7.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
7.2 Reagents: Sodium bicarbonate ; 10 min, rt
8.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
9.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
9.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
9.3 Reagents: Ammonium chloride Solvents: Water
10.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
10.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
10.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
10.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 8
Reaction Conditions + Expand
1.1
Reagents:
Dess-Martin periodinane
Solvents:
Dichloromethane
;
1 h, rt
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
2.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
2.3 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
3.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
3.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
3.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
2.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
2.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
2.3 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
3.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
3.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
3.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 9
Reaction Conditions + Expand
1.1
Reagents:
1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone
,
Thionyl chloride
;
0 °C; 0.5 h, rt
1.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
2.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
3.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
4.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
4.2 Reagents: Sodium bicarbonate ; 10 min, rt
5.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
6.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
6.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
6.3 Reagents: Ammonium chloride Solvents: Water
7.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
7.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
7.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
7.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
1.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
2.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
3.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
4.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
4.2 Reagents: Sodium bicarbonate ; 10 min, rt
5.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
6.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
6.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
6.3 Reagents: Ammonium chloride Solvents: Water
7.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
7.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
7.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
7.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 10
Reaction Conditions + Expand
1.1
Reagents:
2,3-Dichloro-5,6-dicyano-1,4-benzoquinone
Solvents:
Dichloromethane
,
Water
;
2 h, rt
2.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
3.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
3.2 Reagents: Sodium bicarbonate ; 10 min, rt
4.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
5.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
5.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
5.3 Reagents: Ammonium chloride Solvents: Water
6.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
6.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
6.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
6.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
2.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
3.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
3.2 Reagents: Sodium bicarbonate ; 10 min, rt
4.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
5.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
5.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
5.3 Reagents: Ammonium chloride Solvents: Water
6.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
6.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
6.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
6.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 11
Reaction Conditions + Expand
1.1
Reagents:
Lithium diisopropylamide
Solvents:
Tetrahydrofuran
,
Hexane
;
1 h, -78 °C
1.2 Reagents: Triethylsilyl chloride ; 2 h, -78 °C → rt
1.3 Catalysts: Copper(II) triflate , 2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane Solvents: Dichloromethane ; 4 h, rt; rt → -78 °C
1.4 Solvents: Dichloromethane ; 15 h, -78 °C
1.5 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 1 h
2.1 Reagents: 2,6-Lutidine Solvents: Dichloromethane ; 30 min, rt
3.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ; 3 h, 0 °C
3.2 Reagents: Potassium sodium tartrate Solvents: Water
3.3 Reagents: Sulfuric acid Solvents: Water ; pH 4
3.4 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 2 h, rt
3.5 Reagents: Ammonium chloride Solvents: Water
3.6 Catalysts: p-Toluenesulfonic acid ; 1 h, rt
3.7 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Dipyridinium dichromate Solvents: Dichloromethane ; 6 h, rt
5.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
5.2 Reagents: Ammonium chloride Solvents: Water
6.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
6.2 Solvents: Dichloromethane ; 30 min, -78 °C
6.3 Reagents: Triethylamine ; 10 min, -78 °C
6.4 Reagents: Water
7.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
8.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
8.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
9.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
10.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
10.2 Reagents: Ammonium chloride Solvents: Water
11.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
11.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
12.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
13.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
14.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
14.2 Reagents: Sodium bicarbonate ; 10 min, rt
15.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
16.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
16.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
16.3 Reagents: Ammonium chloride Solvents: Water
17.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
17.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
17.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
17.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
1.2 Reagents: Triethylsilyl chloride ; 2 h, -78 °C → rt
1.3 Catalysts: Copper(II) triflate , 2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane Solvents: Dichloromethane ; 4 h, rt; rt → -78 °C
1.4 Solvents: Dichloromethane ; 15 h, -78 °C
1.5 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 1 h
2.1 Reagents: 2,6-Lutidine Solvents: Dichloromethane ; 30 min, rt
3.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ; 3 h, 0 °C
3.2 Reagents: Potassium sodium tartrate Solvents: Water
3.3 Reagents: Sulfuric acid Solvents: Water ; pH 4
3.4 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 2 h, rt
3.5 Reagents: Ammonium chloride Solvents: Water
3.6 Catalysts: p-Toluenesulfonic acid ; 1 h, rt
3.7 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Dipyridinium dichromate Solvents: Dichloromethane ; 6 h, rt
5.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
5.2 Reagents: Ammonium chloride Solvents: Water
6.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
6.2 Solvents: Dichloromethane ; 30 min, -78 °C
6.3 Reagents: Triethylamine ; 10 min, -78 °C
6.4 Reagents: Water
7.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
8.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
8.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
9.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
10.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
10.2 Reagents: Ammonium chloride Solvents: Water
11.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
11.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
12.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
13.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
14.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
14.2 Reagents: Sodium bicarbonate ; 10 min, rt
15.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
16.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
16.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
16.3 Reagents: Ammonium chloride Solvents: Water
17.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
17.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
17.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
17.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 12
Reaction Conditions + Expand
1.1
Reagents:
Dicyclohexylcarbodiimide
Catalysts:
4-(Dimethylamino)pyridine
Solvents:
Dichloromethane
;
5 min, 0 °C; 3 h, rt
2.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran , Hexane ; 1 h, -78 °C
2.2 Reagents: Triethylsilyl chloride ; 2 h, -78 °C → rt
2.3 Catalysts: Copper(II) triflate , 2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane Solvents: Dichloromethane ; 4 h, rt; rt → -78 °C
2.4 Solvents: Dichloromethane ; 15 h, -78 °C
2.5 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 1 h
3.1 Reagents: 2,6-Lutidine Solvents: Dichloromethane ; 30 min, rt
4.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ; 3 h, 0 °C
4.2 Reagents: Potassium sodium tartrate Solvents: Water
4.3 Reagents: Sulfuric acid Solvents: Water ; pH 4
4.4 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 2 h, rt
4.5 Reagents: Ammonium chloride Solvents: Water
4.6 Catalysts: p-Toluenesulfonic acid ; 1 h, rt
4.7 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Dipyridinium dichromate Solvents: Dichloromethane ; 6 h, rt
6.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
6.2 Reagents: Ammonium chloride Solvents: Water
7.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
7.2 Solvents: Dichloromethane ; 30 min, -78 °C
7.3 Reagents: Triethylamine ; 10 min, -78 °C
7.4 Reagents: Water
8.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
9.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
9.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
10.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
11.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
11.2 Reagents: Ammonium chloride Solvents: Water
12.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
12.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
13.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
14.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
15.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
15.2 Reagents: Sodium bicarbonate ; 10 min, rt
16.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
17.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
17.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
17.3 Reagents: Ammonium chloride Solvents: Water
18.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
18.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
18.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
18.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
2.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran , Hexane ; 1 h, -78 °C
2.2 Reagents: Triethylsilyl chloride ; 2 h, -78 °C → rt
2.3 Catalysts: Copper(II) triflate , 2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane Solvents: Dichloromethane ; 4 h, rt; rt → -78 °C
2.4 Solvents: Dichloromethane ; 15 h, -78 °C
2.5 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 1 h
3.1 Reagents: 2,6-Lutidine Solvents: Dichloromethane ; 30 min, rt
4.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ; 3 h, 0 °C
4.2 Reagents: Potassium sodium tartrate Solvents: Water
4.3 Reagents: Sulfuric acid Solvents: Water ; pH 4
4.4 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 2 h, rt
4.5 Reagents: Ammonium chloride Solvents: Water
4.6 Catalysts: p-Toluenesulfonic acid ; 1 h, rt
4.7 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Dipyridinium dichromate Solvents: Dichloromethane ; 6 h, rt
6.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
6.2 Reagents: Ammonium chloride Solvents: Water
7.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
7.2 Solvents: Dichloromethane ; 30 min, -78 °C
7.3 Reagents: Triethylamine ; 10 min, -78 °C
7.4 Reagents: Water
8.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
9.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
9.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
10.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
11.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
11.2 Reagents: Ammonium chloride Solvents: Water
12.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
12.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
13.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
14.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
15.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
15.2 Reagents: Sodium bicarbonate ; 10 min, rt
16.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
17.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
17.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
17.3 Reagents: Ammonium chloride Solvents: Water
18.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
18.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
18.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
18.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 13
Reaction Conditions + Expand
1.1
Reagents:
Dipyridinium dichromate
Solvents:
Dichloromethane
;
6 h, rt
2.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
2.2 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
3.2 Solvents: Dichloromethane ; 30 min, -78 °C
3.3 Reagents: Triethylamine ; 10 min, -78 °C
3.4 Reagents: Water
4.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
5.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
5.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
6.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
7.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
7.2 Reagents: Ammonium chloride Solvents: Water
8.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
8.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
9.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
10.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
11.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
11.2 Reagents: Sodium bicarbonate ; 10 min, rt
12.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
13.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
13.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
13.3 Reagents: Ammonium chloride Solvents: Water
14.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
14.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
14.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
14.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
2.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
2.2 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
3.2 Solvents: Dichloromethane ; 30 min, -78 °C
3.3 Reagents: Triethylamine ; 10 min, -78 °C
3.4 Reagents: Water
4.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
5.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
5.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
6.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
7.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
7.2 Reagents: Ammonium chloride Solvents: Water
8.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
8.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
9.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
10.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
11.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
11.2 Reagents: Sodium bicarbonate ; 10 min, rt
12.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
13.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
13.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
13.3 Reagents: Ammonium chloride Solvents: Water
14.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
14.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
14.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
14.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 14
Reaction Conditions + Expand
1.1
Reagents:
Butyllithium
Solvents:
Tetrahydrofuran
,
Hexane
;
30 min, 0 °C
1.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
1.3 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
2.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
2.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
1.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
1.3 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
2.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
2.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
2.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 15
Reaction Conditions + Expand
1.1
Reagents:
Dimethyl sulfoxide
,
Oxalyl chloride
Solvents:
Dichloromethane
;
20 min, -78 °C
1.2 Solvents: Dichloromethane ; 30 min, -78 °C
1.3 Reagents: Triethylamine ; 10 min, -78 °C
1.4 Reagents: Water
2.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
3.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
3.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
4.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
5.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
5.2 Reagents: Ammonium chloride Solvents: Water
6.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
6.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
7.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
8.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
9.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
9.2 Reagents: Sodium bicarbonate ; 10 min, rt
10.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
11.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
11.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
11.3 Reagents: Ammonium chloride Solvents: Water
12.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
12.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
12.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
12.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
1.2 Solvents: Dichloromethane ; 30 min, -78 °C
1.3 Reagents: Triethylamine ; 10 min, -78 °C
1.4 Reagents: Water
2.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
3.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
3.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
4.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
5.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
5.2 Reagents: Ammonium chloride Solvents: Water
6.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
6.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
7.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
8.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
9.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
9.2 Reagents: Sodium bicarbonate ; 10 min, rt
10.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
11.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
11.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
11.3 Reagents: Ammonium chloride Solvents: Water
12.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
12.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
12.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
12.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 16
Reaction Conditions + Expand
1.1
Reagents:
2,6-Lutidine
Solvents:
Dichloromethane
;
30 min, rt
2.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ; 3 h, 0 °C
2.2 Reagents: Potassium sodium tartrate Solvents: Water
2.3 Reagents: Sulfuric acid Solvents: Water ; pH 4
2.4 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 2 h, rt
2.5 Reagents: Ammonium chloride Solvents: Water
2.6 Catalysts: p-Toluenesulfonic acid ; 1 h, rt
2.7 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Dipyridinium dichromate Solvents: Dichloromethane ; 6 h, rt
4.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
4.2 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
5.2 Solvents: Dichloromethane ; 30 min, -78 °C
5.3 Reagents: Triethylamine ; 10 min, -78 °C
5.4 Reagents: Water
6.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
7.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
7.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
8.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
9.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
9.2 Reagents: Ammonium chloride Solvents: Water
10.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
10.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
11.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
12.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
13.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
13.2 Reagents: Sodium bicarbonate ; 10 min, rt
14.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
15.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
15.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
15.3 Reagents: Ammonium chloride Solvents: Water
16.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
16.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
16.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
16.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
2.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ; 3 h, 0 °C
2.2 Reagents: Potassium sodium tartrate Solvents: Water
2.3 Reagents: Sulfuric acid Solvents: Water ; pH 4
2.4 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 2 h, rt
2.5 Reagents: Ammonium chloride Solvents: Water
2.6 Catalysts: p-Toluenesulfonic acid ; 1 h, rt
2.7 Reagents: Ammonium chloride Solvents: Water
3.1 Reagents: Dipyridinium dichromate Solvents: Dichloromethane ; 6 h, rt
4.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
4.2 Reagents: Ammonium chloride Solvents: Water
5.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
5.2 Solvents: Dichloromethane ; 30 min, -78 °C
5.3 Reagents: Triethylamine ; 10 min, -78 °C
5.4 Reagents: Water
6.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
7.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
7.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
8.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
9.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
9.2 Reagents: Ammonium chloride Solvents: Water
10.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
10.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
11.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
12.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
13.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
13.2 Reagents: Sodium bicarbonate ; 10 min, rt
14.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
15.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
15.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
15.3 Reagents: Ammonium chloride Solvents: Water
16.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
16.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
16.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
16.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 17
Reaction Conditions + Expand
1.1
Catalysts:
Camphorsulfonic acid
Solvents:
Methanol
;
1 h, rt
1.2 Reagents: Sodium bicarbonate ; 10 min, rt
2.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
3.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
3.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
3.3 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
4.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
4.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
4.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
1.2 Reagents: Sodium bicarbonate ; 10 min, rt
2.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
3.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
3.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
3.3 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
4.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
4.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
4.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 18
Reaction Conditions + Expand
1.1
Reagents:
Sodium hydroxide
Solvents:
Methanol
,
Water
;
4 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; pH 3
2.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 5 min, 0 °C; 3 h, rt
3.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran , Hexane ; 1 h, -78 °C
3.2 Reagents: Triethylsilyl chloride ; 2 h, -78 °C → rt
3.3 Catalysts: Copper(II) triflate , 2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane Solvents: Dichloromethane ; 4 h, rt; rt → -78 °C
3.4 Solvents: Dichloromethane ; 15 h, -78 °C
3.5 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 1 h
4.1 Reagents: 2,6-Lutidine Solvents: Dichloromethane ; 30 min, rt
5.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ; 3 h, 0 °C
5.2 Reagents: Potassium sodium tartrate Solvents: Water
5.3 Reagents: Sulfuric acid Solvents: Water ; pH 4
5.4 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 2 h, rt
5.5 Reagents: Ammonium chloride Solvents: Water
5.6 Catalysts: p-Toluenesulfonic acid ; 1 h, rt
5.7 Reagents: Ammonium chloride Solvents: Water
6.1 Reagents: Dipyridinium dichromate Solvents: Dichloromethane ; 6 h, rt
7.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
7.2 Reagents: Ammonium chloride Solvents: Water
8.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
8.2 Solvents: Dichloromethane ; 30 min, -78 °C
8.3 Reagents: Triethylamine ; 10 min, -78 °C
8.4 Reagents: Water
9.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
10.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
10.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
11.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
12.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
12.2 Reagents: Ammonium chloride Solvents: Water
13.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
13.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
14.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
15.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
16.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
16.2 Reagents: Sodium bicarbonate ; 10 min, rt
17.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
18.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
18.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
18.3 Reagents: Ammonium chloride Solvents: Water
19.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
19.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
19.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
19.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
1.2 Reagents: Hydrochloric acid Solvents: Water ; pH 3
2.1 Reagents: Dicyclohexylcarbodiimide Catalysts: 4-(Dimethylamino)pyridine Solvents: Dichloromethane ; 5 min, 0 °C; 3 h, rt
3.1 Reagents: Lithium diisopropylamide Solvents: Tetrahydrofuran , Hexane ; 1 h, -78 °C
3.2 Reagents: Triethylsilyl chloride ; 2 h, -78 °C → rt
3.3 Catalysts: Copper(II) triflate , 2,2-Bis[2-[4(S)-tert-butyl-1,3-oxazolinyl]]propane Solvents: Dichloromethane ; 4 h, rt; rt → -78 °C
3.4 Solvents: Dichloromethane ; 15 h, -78 °C
3.5 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 1 h
4.1 Reagents: 2,6-Lutidine Solvents: Dichloromethane ; 30 min, rt
5.1 Reagents: Lithium aluminum hydride Solvents: Tetrahydrofuran ; 3 h, 0 °C
5.2 Reagents: Potassium sodium tartrate Solvents: Water
5.3 Reagents: Sulfuric acid Solvents: Water ; pH 4
5.4 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 2 h, rt
5.5 Reagents: Ammonium chloride Solvents: Water
5.6 Catalysts: p-Toluenesulfonic acid ; 1 h, rt
5.7 Reagents: Ammonium chloride Solvents: Water
6.1 Reagents: Dipyridinium dichromate Solvents: Dichloromethane ; 6 h, rt
7.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
7.2 Reagents: Ammonium chloride Solvents: Water
8.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
8.2 Solvents: Dichloromethane ; 30 min, -78 °C
8.3 Reagents: Triethylamine ; 10 min, -78 °C
8.4 Reagents: Water
9.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
10.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
10.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
11.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
12.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
12.2 Reagents: Ammonium chloride Solvents: Water
13.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
13.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
14.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
15.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
16.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
16.2 Reagents: Sodium bicarbonate ; 10 min, rt
17.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
18.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
18.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
18.3 Reagents: Ammonium chloride Solvents: Water
19.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
19.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
19.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
19.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 19
Reaction Conditions + Expand
1.1
Reagents:
Lithium aluminum hydride
Solvents:
Tetrahydrofuran
;
3 h, 0 °C
1.2 Reagents: Potassium sodium tartrate Solvents: Water
1.3 Reagents: Sulfuric acid Solvents: Water ; pH 4
1.4 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 2 h, rt
1.5 Reagents: Ammonium chloride Solvents: Water
1.6 Catalysts: p-Toluenesulfonic acid ; 1 h, rt
1.7 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Dipyridinium dichromate Solvents: Dichloromethane ; 6 h, rt
3.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
3.2 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
4.2 Solvents: Dichloromethane ; 30 min, -78 °C
4.3 Reagents: Triethylamine ; 10 min, -78 °C
4.4 Reagents: Water
5.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
6.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
6.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
7.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
8.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
8.2 Reagents: Ammonium chloride Solvents: Water
9.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
9.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
10.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
11.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
12.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
12.2 Reagents: Sodium bicarbonate ; 10 min, rt
13.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
14.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
14.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
14.3 Reagents: Ammonium chloride Solvents: Water
15.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
15.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
15.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
15.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
1.2 Reagents: Potassium sodium tartrate Solvents: Water
1.3 Reagents: Sulfuric acid Solvents: Water ; pH 4
1.4 Reagents: Tetrabutylammonium fluoride Solvents: Tetrahydrofuran ; 2 h, rt
1.5 Reagents: Ammonium chloride Solvents: Water
1.6 Catalysts: p-Toluenesulfonic acid ; 1 h, rt
1.7 Reagents: Ammonium chloride Solvents: Water
2.1 Reagents: Dipyridinium dichromate Solvents: Dichloromethane ; 6 h, rt
3.1 Solvents: Tetrahydrofuran ; 0 °C; 1 h, rt
3.2 Reagents: Ammonium chloride Solvents: Water
4.1 Reagents: Dimethyl sulfoxide , Oxalyl chloride Solvents: Dichloromethane ; 20 min, -78 °C
4.2 Solvents: Dichloromethane ; 30 min, -78 °C
4.3 Reagents: Triethylamine ; 10 min, -78 °C
4.4 Reagents: Water
5.1 Reagents: 2-Methyl-2-butene , Monosodium phosphate , Sodium chlorite Solvents: tert-Butanol , Water ; rt; 2 h, rt
6.1 Reagents: Triethylamine , Isobutyl chloroformate Solvents: Diethyl ether , Tetrahydrofuran ; 30 min, -20 °C; -20 °C → 0 °C
6.2 Solvents: Diethyl ether ; 0 °C; 3 h, rt
7.1 Reagents: (Trifluoromethyl)benzene Catalysts: Rhodium, tetrakis[μ-[(αS)-1,3-dihydro-α-(1-methylethyl)-1,3-dioxo-2H-benz[f]isoi… ; 3 h, -40 °C
8.1 Solvents: Tetrahydrofuran ; 1 h, -20 °C
8.2 Reagents: Ammonium chloride Solvents: Water
9.1 Reagents: 1,3-Dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone , Thionyl chloride ; 0 °C; 0.5 h, rt
9.2 Reagents: Sodium Solvents: Diethyl ether ; 12 h, reflux
10.1 Reagents: 2,3-Dichloro-5,6-dicyano-1,4-benzoquinone Solvents: Dichloromethane , Water ; 2 h, rt
11.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
12.1 Catalysts: Camphorsulfonic acid Solvents: Methanol ; 1 h, rt
12.2 Reagents: Sodium bicarbonate ; 10 min, rt
13.1 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
14.1 Reagents: Butyllithium Solvents: Tetrahydrofuran , Hexane ; 30 min, 0 °C
14.2 Solvents: Tetrahydrofuran ; 5 h, 0 °C → rt
14.3 Reagents: Ammonium chloride Solvents: Water
15.1 Reagents: Acetic acid Solvents: Water ; 0.5 h, 60 °C; 60 °C → rt
15.2 Reagents: Sodium bicarbonate Solvents: Water ; pH 7
15.3 Reagents: Dess-Martin periodinane Solvents: Dichloromethane ; 1 h, rt
15.4 Reagents: Hydrochloric acid Solvents: Tetrahydrofuran , Water ; 7 h, rt
Reference
Total synthesis of pseudolaric acid A
, Angewandte Chemie, 2006, 45(37), 6197-6201
- 1. Pseudolaric acids: isolation, bioactivity and synthetic studies Pauline Chiu,Lai To Leung,Ben C. B. Ko Nat. Prod. Rep. 2010 27 1066
-
Methylpseudolarate B CAS No.: 82508-34-7 -
Pseudolaric acid B CAS No.: 82508-31-4 -
-
Pseudolaric Acid C CAS No.: 82601-41-0 -
-
Methyl pseudolarate A CAS No.: 82508-33-6
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