Pseudolaric acid B is a diterpenoid acid isolated from the root of Pseudolarix kaempferi (Pinaceae). It has anticancer \ antifungal \ antifertility activities and immunosuppressive activity on T lymphocytes Conclusion: Pseudolaric acid B inhibits the secretion of hepatitis B virus (HBV) through apoptosis and cell cycle arrest Pseudolaric acid B induces autophagy
Synthetic Circuit 1
Reaction Conditions + Expand
1.1
Catalysts:
Scandium triflate
Solvents:
Acetic anhydride
;
2 h, 0 °C
2.1
Catalysts:
Dichlorobis(triphenylphosphine)palladium
Solvents:
Tetrahydrofuran
;
15 min, rt
3.1
Reagents:
Diisopropylethylamine
Catalysts:
Tris(dibenzylideneacetone)dipalladium
Solvents:
N-Methyl-2-pyrrolidone
;
17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557
Synthetic Circuit 2
Reaction Conditions + Expand
1.1
Reagents:
Zinc acetate
Solvents:
Methanol
,
Chloroform
;
16 h, 60 °C
2.1
Reagents:
Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine
Catalysts:
Sodium ascorbate
,
Copper sulfate
Solvents:
Methanol
,
Chloroform
,
Dimethyl sulfoxide
,
Water
;
4 h, 30 °C
3.1
Solvents:
Dimethyl sulfoxide
,
Water
;
300 s, pH 7.4, rt
Reference
Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids
Watanabe, Kenji ; et al, Journal of Organic Chemistry, 2021, 86(17), 11822-11834
Synthetic Circuit 3
Reaction Conditions + Expand
1.1
Catalysts:
Dichlorobis(triphenylphosphine)palladium
Solvents:
Tetrahydrofuran
;
15 min, rt
2.1
Reagents:
Diisopropylethylamine
Catalysts:
Tris(dibenzylideneacetone)dipalladium
Solvents:
N-Methyl-2-pyrrolidone
;
17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557
Synthetic Circuit 4
Reaction Conditions + Expand
1.1
Reagents:
Sodium hydride
Solvents:
Diethyl ether
;
15 min, rt; 3 h, reflux; reflux → 23 °C
1.2
23 °C; 20 h, reflux; reflux → 0 °C
1.3
Reagents:
Hydrochloric acid
Solvents:
Water
;
0 °C
2.1
Reagents:
Potassium hydroxide
Solvents:
Ethanol
,
Water
;
rt; 20 h, reflux; reflux → 23 °C
3.1
Reagents:
Diisopropylethylamine
Catalysts:
Tris(dibenzylideneacetone)dipalladium
Solvents:
N-Methyl-2-pyrrolidone
;
rt; 22 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2008, 130(48), 16424-16434
Synthetic Circuit 5
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
3.1
Reagents:
4-(Dimethylamino)pyridine
;
8 h, rt
4.1
-
Reference
Total synthesis of pseudolaric acid A
Geng, Zhe; et al, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 6
Reaction Conditions + Expand
1.1
Reagents:
1-Ethyl-3-(3′-dimethylaminopropyl)carbodiimide hydrochloride
Catalysts:
4-(Dimethylamino)pyridine
Solvents:
Dimethylformamide
;
20 h, 30 °C
2.1
Reagents:
Zinc acetate
Solvents:
Methanol
,
Chloroform
;
16 h, 60 °C
3.1
Reagents:
Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine
Catalysts:
Sodium ascorbate
,
Copper sulfate
Solvents:
Methanol
,
Chloroform
,
Dimethyl sulfoxide
,
Water
;
4 h, 30 °C
4.1
Solvents:
Dimethyl sulfoxide
,
Water
;
300 s, pH 7.4, rt
Reference
Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids
Watanabe, Kenji ; et al, Journal of Organic Chemistry, 2021, 86(17), 11822-11834
Synthetic Circuit 7
Reaction Conditions + Expand
1.1
Reagents:
Potassium hydroxide
Solvents:
Ethanol
,
Water
;
20 h, reflux; reflux → 23 °C
1.2
Reagents:
Potassium carbonate
,
Hydrochloric acid
Solvents:
Dichloromethane
,
Water
;
pH 1, 23 °C
2.1
Reagents:
Diisopropylethylamine
Catalysts:
Tris(dibenzylideneacetone)dipalladium
Solvents:
N-Methyl-2-pyrrolidone
;
17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557
Synthetic Circuit 8
Reaction Conditions + Expand
1.1
Reagents:
Hydrochloric acid
Solvents:
Methanol
Reference
Thermodynamic theory of gases on solid interface adsorption isotherms
Li, Xueliang; et al, Huaxue Tongbao, 1995, (7), 57-61
Synthetic Circuit 9
Reaction Conditions + Expand
Reference
Total synthesis of pseudolaric acid A
Geng, Zhe; et al, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 10
Reaction Conditions + Expand
1.1
Reagents:
Tetrabutylammonium fluoride
Solvents:
Tetrahydrofuran
;
0 °C; 20 min, 23 °C
2.1
Catalysts:
Scandium triflate
Solvents:
Acetic anhydride
;
2 h, 0 °C
3.1
Catalysts:
Dichlorobis(triphenylphosphine)palladium
Solvents:
Tetrahydrofuran
;
15 min, rt
4.1
Reagents:
Diisopropylethylamine
Catalysts:
Tris(dibenzylideneacetone)dipalladium
Solvents:
N-Methyl-2-pyrrolidone
;
17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557
Synthetic Circuit 11
Reaction Conditions + Expand
1.1
Reagents:
Dess-Martin periodinane
Solvents:
Dichloromethane
;
30 min, rt
2.1
-
Reference
Formal Synthesis of Pseudolaric Acid B
Mori, Naoki, Synlett, 2020, 31(9), 907-910
Synthetic Circuit 12
Reaction Conditions + Expand
1.1
Reagents:
4-(Dimethylamino)pyridine
;
8 h, rt
2.1
-
Reference
Total synthesis of pseudolaric acid A
Geng, Zhe; et al, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 13
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
2.1
Reagents:
4-(Dimethylamino)pyridine
;
8 h, rt
3.1
-
Reference
Total synthesis of pseudolaric acid A
Geng, Zhe; et al, Angewandte Chemie, 2006, 45(37), 6197-6201
Synthetic Circuit 14
Reaction Conditions + Expand
1.1
Reagents:
Diisopropylethylamine
Catalysts:
Tris(dibenzylideneacetone)dipalladium
Solvents:
N-Methyl-2-pyrrolidone
;
17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557
Synthetic Circuit 15
Reaction Conditions + Expand
1.1
Reagents:
Tris[(1-benzyl-1H-1,2,3-triazol-4-yl)methyl]amine
Catalysts:
Sodium ascorbate
,
Copper sulfate
Solvents:
Methanol
,
Chloroform
,
Dimethyl sulfoxide
,
Water
;
4 h, 30 °C
2.1
Solvents:
Dimethyl sulfoxide
,
Water
;
300 s, pH 7.4, rt
Reference
Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids
Watanabe, Kenji ; et al, Journal of Organic Chemistry, 2021, 86(17), 11822-11834
Synthetic Circuit 16
Reaction Conditions + Expand
1.1
Catalysts:
Dichlorobis(triphenylphosphine)palladium
Solvents:
Tetrahydrofuran
;
rt; 15 min, rt
2.1
Reagents:
Diisopropylethylamine
Catalysts:
Tris(dibenzylideneacetone)dipalladium
Solvents:
N-Methyl-2-pyrrolidone
;
rt; 22 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2008, 130(48), 16424-16434
Synthetic Circuit 17
Reaction Conditions + Expand
1.1
Solvents:
Dimethyl sulfoxide
,
Water
;
300 s, pH 7.4, rt
Reference
Direct 3-Acylation of Indolizines by Carboxylic Acids for the Practical Synthesis of Red Light-Releasable Caged Carboxylic Acids
Watanabe, Kenji ; et al, Journal of Organic Chemistry, 2021, 86(17), 11822-11834
Synthetic Circuit 18
Reaction Conditions + Expand
1.1
Catalysts:
Scandium triflate
Solvents:
Acetic anhydride
;
0 °C; 2 h, 0 °C
2.1
Catalysts:
Dichlorobis(triphenylphosphine)palladium
Solvents:
Tetrahydrofuran
;
rt; 15 min, rt
3.1
Reagents:
Diisopropylethylamine
Catalysts:
Tris(dibenzylideneacetone)dipalladium
Solvents:
N-Methyl-2-pyrrolidone
;
rt; 22 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2008, 130(48), 16424-16434
Synthetic Circuit 19
Reaction Conditions + Expand
1.1
Reagents:
Cerium trichloride
Solvents:
Diethyl ether
,
Tetrahydrofuran
;
30 min, -78 °C
1.2
Solvents:
Tetrahydrofuran
;
1 h, -78 °C
1.3
Reagents:
Ammonium chloride
Solvents:
Water
2.1
Reagents:
Dess-Martin periodinane
Solvents:
Dichloromethane
;
30 min, rt
3.1
-
Reference
Formal Synthesis of Pseudolaric Acid B
Mori, Naoki, Synlett, 2020, 31(9), 907-910
Synthetic Circuit 20
Reaction Conditions + Expand
1.1
Reagents:
Sodium hydride
Solvents:
Diethyl ether
;
3 h, reflux; reflux → 23 °C
1.2
20 h, reflux; reflux → 0 °C
1.3
Reagents:
Hydrochloric acid
Solvents:
Water
;
0 °C
2.1
Reagents:
Potassium hydroxide
Solvents:
Ethanol
,
Water
;
20 h, reflux; reflux → 23 °C
2.2
Reagents:
Potassium carbonate
,
Hydrochloric acid
Solvents:
Dichloromethane
,
Water
;
pH 1, 23 °C
3.1
Reagents:
Diisopropylethylamine
Catalysts:
Tris(dibenzylideneacetone)dipalladium
Solvents:
N-Methyl-2-pyrrolidone
;
17 h, rt; 5 h, rt
Reference
Total Synthesis of (-)-Pseudolaric Acid B
Trost, Barry M.; et al, Journal of the American Chemical Society, 2007, 129(47), 14556-14557