Multi-step reaction with 17 steps
1: 86 percent / NaOCH3 / methanol; CH2Cl2 / 0 °C
2: 73 percent / CuSO4
3: 92 percent / pyridine / CH2Cl2 / 0 °C
4: 65 percent / aq. H2NOH*HCl; NaOAc / ethanol / Heating
5: 86 percent / aq. OsO4; NMO / tetrahydrofuran / 20 °C
6: 95 percent / imidazole / dimethylformamide / 20 °C
7: 81 percent / pyridine
8: TBAF / tetrahydrofuran
9: Bu4N+AcO- / butan-2-one / Heating
10: 71 percent / aq. AcOH / tetrahydrofuran / 40 °C
11: 76 percent / DMAP / 0 - 20 °C
12: 84 percent / tetrahydrofuran / -78 °C
13: 69 percent / DMAP / dimethylformamide / 48 h / 85 °C
14: 90 percent / DCC; DMAP / toluene
15: 83 percent / NaBH4 / methanol / 20 °C
16: 86 percent / DCC; DMAP / toluene
17: 73 percent / H2 / 10 percent Pd/C / ethyl acetate / 20 °C
With
pyridine; 1H-imidazole; dmap; sodium tetrahydroborate; osmium(VIII) oxide; N-methyl-2-indolinone; hydroxylamine hydrochloride; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; sodium acetate; tetrabutylammonium acetate; copper(II) sulfate; acetic acid; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; toluene; butanone;
1: Deacetylation / 2: ketalization / 3: cyclocondensation / 4: Hydrolysis / 5: dihydroxylation / 6: silylation / 7: mesylation / 8: desilylation / 9: Cyclization / 10: deketalization / 11: Acetylation / 12: Addition / 13: Addition / 14: Esterification / 15: Reduction / 16: Esterification / 17: Hydrogenolysis;
DOI:10.1016/S0960-894X(00)00031-7