Technology Process of 11β-phenylselenyl-4α-hydroxy-5,7αH,8βH-guai-1(10)-en-8,12-olide
There total 14 articles about 11β-phenylselenyl-4α-hydroxy-5,7αH,8βH-guai-1(10)-en-8,12-olide which
guide to synthetic route it.
The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:
synthetic route:
- Guidance literature:
-
4α-hydroxy-5,7,11αH,8βH-guai-1(10)-en-8,12-olide;
With
lithium diisopropyl amide;
In
tetrahydrofuran;
at -78 ℃;
for 1h;
Phenylselenyl chloride;
In
tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;
at -78 - -30 ℃;
Further stages.;
DOI:10.1021/jo991756n
- Guidance literature:
-
Multi-step reaction with 12 steps
1.1: 90 percent / DMAP / pyridine / 3 h / 20 °C
2.1: 54 percent / 9 h / Irradiation
3.1: 74 percent / H2 / Pd/C / ethanol / 2.5 h
4.1: 56 percent / NaBH4 / methanol / 0.33 h / 0 °C
5.1: Et3N / CH2Cl2 / 3 h / 0 °C
6.1: 178 mg / Li2CO3 / dimethylformamide / 2 h / 100 °C
7.1: KOH / methanol / 2 h / 20 °C
7.2: 98 percent / 2M HCl
8.1: 53 percent / magnesium monoperphthalate / methanol / 5 h / 20 °C
9.1: 66 percent / Tf2O; pyridine / CH2Cl2 / 29 h / 20 °C
10.1: 81 percent / AcOH; Ti(i-PrO)4 / dimethylformamide; CH2Cl2 / 7 h
11.1: 95 percent / deactivated ethanolic W-2 Raney Ni / methanol / 1 h / 20 °C
12.1: LDA / tetrahydrofuran / 1 h / -78 °C
12.2: 56 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -30 °C
With
pyridine; titanium(IV) isopropylate; dmap; potassium hydroxide; sodium tetrahydroborate; trifluoromethylsulfonic anhydride; deactivated ethanolic W-2 Raney Ni; hydrogen; lithium carbonate; magnesium monoperoxyphthalate hexahydrate; acetic acid; triethylamine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
1.1: Acetylation / 2.1: Acetoxylation / 3.1: Catalytic hydrogenation / 4.1: Reduction / 5.1: Substitution / 6.1: Elimination / 7.1: Hydrolysis / 7.2: lactonization / 8.1: Epoxidation / 9.1: Elimination / 10.1: Ring cleavage / 11.1: reductive elimination / 12.1: Metallation / 12.2: Substitution;
DOI:10.1021/jo991756n
- Guidance literature:
-
Multi-step reaction with 11 steps
1.1: 54 percent / 9 h / Irradiation
2.1: 74 percent / H2 / Pd/C / ethanol / 2.5 h
3.1: 56 percent / NaBH4 / methanol / 0.33 h / 0 °C
4.1: Et3N / CH2Cl2 / 3 h / 0 °C
5.1: 178 mg / Li2CO3 / dimethylformamide / 2 h / 100 °C
6.1: KOH / methanol / 2 h / 20 °C
6.2: 98 percent / 2M HCl
7.1: 53 percent / magnesium monoperphthalate / methanol / 5 h / 20 °C
8.1: 66 percent / Tf2O; pyridine / CH2Cl2 / 29 h / 20 °C
9.1: 81 percent / AcOH; Ti(i-PrO)4 / dimethylformamide; CH2Cl2 / 7 h
10.1: 95 percent / deactivated ethanolic W-2 Raney Ni / methanol / 1 h / 20 °C
11.1: LDA / tetrahydrofuran / 1 h / -78 °C
11.2: 56 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -78 - -30 °C
With
pyridine; titanium(IV) isopropylate; potassium hydroxide; sodium tetrahydroborate; trifluoromethylsulfonic anhydride; deactivated ethanolic W-2 Raney Ni; hydrogen; lithium carbonate; magnesium monoperoxyphthalate hexahydrate; acetic acid; triethylamine; lithium diisopropyl amide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; N,N-dimethyl-formamide;
1.1: Acetoxylation / 2.1: Catalytic hydrogenation / 3.1: Reduction / 4.1: Substitution / 5.1: Elimination / 6.1: Hydrolysis / 6.2: lactonization / 7.1: Epoxidation / 8.1: Elimination / 9.1: Ring cleavage / 10.1: reductive elimination / 11.1: Metallation / 11.2: Substitution;
DOI:10.1021/jo991756n
