Multi-step reaction with 10 steps
1.1: O2; Rose Bengal / acetone / 8 h / -10 °C / Irradiation
1.2: RuCl2(PPh3)3 / CH2Cl2 / -10 - 20 °C
1.3: 42 percent / NaOMe / methanol / 0.5 h / -5 °C
2.1: 99 percent / Et3N; 4-dimethylaminopyridine / CH2Cl2 / 0 - 20 °C
3.1: 80 percent Turnov. / cholesterol esterase; aq. NaOH / 36 h / 5 °C / pH 7.7
4.1: 98 percent / imidazole / dimethylformamide / 0.67 h / 20 °C
5.1: 81 percent Turnov. / LiOH*H2O / methanol / 48 h / -5 °C
6.1: diphenylphosphorazidate; Et3N / benzene / 1 h
6.2: toluene / 1 h / 110 °C
7.1: n-BuLi / tetrahydrofuran; pentane / 0.5 h / -100 °C
7.2: tetrahydrofuran; toluene; pentane / 0.75 h / -100 °C
8.1: NaH / dimethylformamide / 0.5 h / -5 °C
8.2: dimethylformamide / 0.25 h / -5 °C
9.1: 76 percent / pyridinium p-toluenesulfonate / methanol / 2 h / 20 °C
10.1: 30 percent / benzene / 48 h / 5 °C / UV-irradiation
With
1H-imidazole; dmap; lithium hydroxide; sodium hydroxide; n-butyllithium; cholesterol esterase; diphenyl phosphoryl azide; oxygen; pyridinium p-toluenesulfonate; rose bengal; sodium hydride; triethylamine;
In
tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; pentane; benzene;
1.1: Oxidation / 1.2: Epoxidation / 1.3: Ring cleavage / 2.1: Acylation / 3.1: Hydrolysis / 4.1: silylation / 5.1: Hydrolysis / 6.1: azidation / 6.2: Rearrangement / 7.1: Metallation / 7.2: Addition / 8.1: Metallation / 8.2: Substitution / 9.1: deprotection / 10.1: Cyclization;
DOI:10.1021/ja000930i