Multi-step reaction with 15 steps
1.1: sodium hydride / tetrahydrofuran; mineral oil / 0.17 h / 0 °C / Inert atmosphere
2.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / hexanes; diethyl ether / 15 h / Inert atmosphere; Cooling
2.2: 0.25 h / Inert atmosphere; Cooling
2.3: 20 °C / Inert atmosphere; Cooling
3.1: boron trifluoride diethyl etherate / dichloromethane / 0.13 h / -78 °C / Inert atmosphere
3.2: 23 h / 20 °C / 760.05 Torr
4.1: manganese(IV) oxide / dichloromethane / 20 h / 20 °C / Inert atmosphere
5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 2 h / 20 °C / Inert atmosphere
5.2: 20 h / 20 °C / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 2 h / 20 °C / Inert atmosphere
7.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 26 h / 20 °C / Inert atmosphere
8.1: potassium hydroxide / ethanol / 0.42 h / 20 °C / Inert atmosphere
9.1: sodium tetrahydroborate; cerium(III) chloride heptahydrate / dichloromethane / 2 h / 20 °C / Inert atmosphere
10.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / 1,4-dioxane; tert-butyl alcohol / 17 h / 20 °C
11.1: sodium periodate; water / dichloromethane / 24 h / 20 °C
12.1: sodium tetrahydroborate / tetrahydrofuran; methanol / 0.25 h / 20 °C / Inert atmosphere
13.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran; water / 0.25 h / 20 °C
14.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 5.33 h / 20 °C / Inert atmosphere
15.1: n-butyllithium; diisopropylamine / tetrahydrofuran; hexanes / 0.08 h / Inert atmosphere; Cooling with ice
15.2: 2 h / Inert atmosphere; Cooling with ice
15.3: 2 h / Inert atmosphere; Cooling with ice
With
manganese(IV) oxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; n-butyllithium; tetrapropylammonium perruthennate; N,N,N,N,-tetramethylethylenediamine; cerium(III) chloride heptahydrate; boron trifluoride diethyl etherate; water; sodium hydride; 4-methylmorpholine N-oxide; diisopropylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; methanol; hexanes; diethyl ether; ethanol; dichloromethane; water; mineral oil; tert-butyl alcohol;
DOI:10.1021/jo1022102