Multi-step reaction with 20 steps
1.1: sodium tetrahydroborate / ethanol / 2 h / -78 °C / Inert atmosphere
2.1: dichloromethane / 1 h / 20 °C / Inert atmosphere; Molecular sieve
2.2: 39 h / 20 °C / Inert atmosphere
3.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
4.1: 2,6-di-tert-butyl-4-methylpyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetonitrile / 20 °C / Inert atmosphere
5.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / -40 - -30 °C / Inert atmosphere
6.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 13 °C / Inert atmosphere
7.1: lithium borohydride / tetrahydrofuran / Inert atmosphere; Reflux
7.2: 4 h / 20 °C / Inert atmosphere
8.1: lithium borohydride / tetrahydrofuran / 26.5 h / 20 °C / Inert atmosphere; Reflux
8.2: 4 h / 20 °C / Inert atmosphere
9.1: water; acetic acid / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
10.1: dmap / pyridine; dichloromethane / 24 h / 20 °C / Inert atmosphere
11.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
12.1: peracetic acid; mercury(II) diacetate; acetic acid / 4 h / 20 °C / Inert atmosphere
13.1: 1H-imidazole / dichloromethane / 4 h / 0 °C / Inert atmosphere
14.1: dmap / pyridine; dichloromethane / 0 - 40 °C / Inert atmosphere
15.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
16.1: Dess-Martin periodane / dichloromethane / 0 - 20 °C / Inert atmosphere
17.1: Wilkinson's catalyst; triphenylphosphine; isopropyl alcohol / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere
18.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 5 h / 20 °C / Inert atmosphere
19.1: di(n-butyl)tin oxide / benzene / 16 h / Reflux; Inert atmosphere
19.2: 0.17 h / 20 °C / Inert atmosphere; Molecular sieve
20.1: triethylamine / benzene / 24 h / 20 °C / Inert atmosphere
With
1H-imidazole; peracetic acid; dmap; sodium tetrahydroborate; Wilkinson's catalyst; osmium(VIII) oxide; lithium borohydride; 2,6-di-tert-butyl-4-methylpyridine; mercury(II) diacetate; tetrabutyl ammonium fluoride; water; di(n-butyl)tin oxide; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; 4-methylmorpholine N-oxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; pyridine; ethanol; dichloromethane; water; acetone; acetonitrile; benzene;
5.1: Luche reduction / 12.1: Tamao oxidation;
DOI:10.1002/asia.200800429