Multi-step reaction with 14 steps
1.1: 70 percent / NH2OH*HCl; NaOAc / ethanol; H2O / 24 h / 80 °C
2.1: 81 percent / pyridine / 0.67 h / 20 °C
3.1: 81 percent / NaOMe / CH2Cl2; methanol / 24 h / 0 °C
4.1: 88 percent / pyridine / CH2Cl2 / 0.5 h / 0 °C
5.1: 100 percent / TBAF / tetrahydrofuran / 1 h / 20 °C
6.1: 83 percent / OsO4; N-methylmorpholine N-oxide / tetrahydrofuran; H2O; 2-methyl-propan-2-ol / 20 h / 20 °C
7.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C
8.1: 83 percent / pyridine / 20 h / 20 °C
9.1: TBAF / tetrahydrofuran / 1 h / 20 °C
9.2: 76 percent / TBAOAc / butan-2-one / 20 h / Heating
10.1: 93 percent / DMAP / CH2Cl2 / 5 h / 20 °C
11.1: 64 percent / tetrahydrofuran; cyclohexane; diethyl ether / 0.33 h / -78 °C
12.1: 70 percent / n-methylmorpholine N-oxide; tetrapropylammonium perruthenate / CH2Cl2 / 3 h / 20 °C
13.1: 74 percent / NaBH4 / methanol / 3 h / 20 °C
14.1: DMAP; DCC / toluene / 1.5 h / 75 °C
14.2: 78 percent / TFA / H2O / 0.67 h / 0 - 20 °C
With
pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; tetrapropylammonium perruthennate; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; sodium methylate; sodium acetate; 4-methylmorpholine N-oxide; dicyclohexyl-carbodiimide;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
1.1: Hydrolysis / 2.1: silylation / 3.1: Deacetylation / 4.1: Carbonylation / 5.1: desilylation / 6.1: Oxidation / 7.1: silylation / 8.1: mesylation / 9.1: desylilation / 9.2: Cyclization / 10.1: Acetylation / 11.1: Phenylation / 12.1: Oxidation / 13.1: Reduction / 14.1: Esterification / 14.2: Hydrolysis;
DOI:10.1016/S0040-4020(00)00073-9