Multi-step reaction with 12 steps
1.1: 2,6-di-tert-butyl-4-methylpyridine; 2,3-dicyano-5,6-dichloro-p-benzoquinone / acetonitrile / 20 °C / Inert atmosphere
2.1: sodium tetrahydroborate / tetrahydrofuran; ethanol / -40 - -30 °C / Inert atmosphere
3.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 13 °C / Inert atmosphere
4.1: lithium borohydride / tetrahydrofuran / Inert atmosphere; Reflux
4.2: 4 h / 20 °C / Inert atmosphere
5.1: lithium borohydride / tetrahydrofuran / 26.5 h / 20 °C / Inert atmosphere; Reflux
5.2: 4 h / 20 °C / Inert atmosphere
6.1: water; acetic acid / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere
7.1: dmap / pyridine; dichloromethane / 24 h / 20 °C / Inert atmosphere
8.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere
9.1: peracetic acid; mercury(II) diacetate; acetic acid / 4 h / 20 °C / Inert atmosphere
10.1: 1H-imidazole / dichloromethane / 4 h / 0 °C / Inert atmosphere
11.1: dmap / pyridine; dichloromethane / 0 - 40 °C / Inert atmosphere
12.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
With
1H-imidazole; peracetic acid; dmap; sodium tetrahydroborate; lithium borohydride; 2,6-di-tert-butyl-4-methylpyridine; mercury(II) diacetate; tetrabutyl ammonium fluoride; water; sodium hydrogencarbonate; acetic acid; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone;
In
tetrahydrofuran; pyridine; ethanol; dichloromethane; acetonitrile;
2.1: Luche reduction / 9.1: Tamao oxidation;
DOI:10.1002/asia.200800429