Multi-step reaction with 11 steps
1.1: lithium borohydride / diethyl ether / 20.5 h / 0 °C / Inert atmosphere
2.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
3.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / hexanes; diethyl ether / 15 h / Inert atmosphere; Cooling
3.2: 0.25 h / Inert atmosphere; Cooling
3.3: 20 °C / Inert atmosphere; Cooling
4.1: boron trifluoride diethyl etherate / dichloromethane / 0.13 h / -78 °C / Inert atmosphere
4.2: 23 h / 20 °C / 760.05 Torr
5.1: manganese(IV) oxide / dichloromethane / 20 h / 20 °C / Inert atmosphere
6.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere
6.2: 20 h / 20 °C / Inert atmosphere
7.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere
8.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 26 h / 20 °C / Inert atmosphere
9.1: potassium hydroxide / ethanol / 0.42 h / 20 °C / Inert atmosphere
10.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / dichloromethane / 2 h / 20 °C / Inert atmosphere
11.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / 1,4-dioxane; tert-butyl alcohol / 17 h / 20 °C
With
manganese(IV) oxide; sodium tetrahydroborate; osmium(VIII) oxide; lithium borohydride; n-butyllithium; tetrapropylammonium perruthennate; N,N,N,N,-tetramethylethylenediamine; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; water; sodium hydride; 4-methylmorpholine N-oxide; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; potassium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; hexanes; diethyl ether; ethanol; dichloromethane; mineral oil; tert-butyl alcohol;
DOI:10.1021/jo1022102