Multi-step reaction with 14 steps
1.1: toluene / Reflux
2.1: pyridinium perbromide hydrobromide / tetrahydrofuran; chloroform / 2.33 h / -10 °C
3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0 - 20 °C
3.2: 4 h / 0 - 20 °C
4.1: hydrazine hydrate / ethanol / Reflux
5.1: methanol / 24 h / 20 °C
6.1: boron trifluoride diethyl etherate / tetrahydrofuran; dichloromethane / 0.25 h / -40 °C / Inert atmosphere
6.2: 4 h / -40 - 20 °C
7.1: sodium hydride / tetrahydrofuran; mineral oil / 0.5 h / 0 °C / Inert atmosphere
7.2: 0 °C
8.1: tert.-butyl lithium / diethyl ether; pentane / 1.5 h / -40 - 20 °C / Inert atmosphere
9.1: sodium disulfate / tetrahydrofuran / 5 h / 23 °C
9.2: 3 h
10.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water; tert-butyl alcohol / 20 °C
10.2: 2 h / 20 °C
11.1: sodium cyanoborohydride / tetrahydrofuran; acetic acid / 1 h / 0 °C
12.1: triethylamine / dichloromethane / 0 - 20 °C / Inert atmosphere
13.1: sodium azide / N,N-dimethyl-formamide / 95 °C
14.1: triphenylphosphine / toluene / Reflux
With
osmium(VIII) oxide; sodium azide; sodium disulfate; pyridinium perbromide hydrobromide; boron trifluoride diethyl etherate; tert.-butyl lithium; sodium hydride; sodium cyanoborohydride; hydrazine hydrate; 4-methylmorpholine N-oxide; triethylamine; triphenylphosphine;
In
tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; chloroform; water; acetic acid; N,N-dimethyl-formamide; toluene; mineral oil; tert-butyl alcohol; pentane;
14.1: Aza-Wittig reaction;
DOI:10.1021/ol202475r