Multi-step reaction with 11 steps
1.1: boron trifluoride diethyl etherate; sodium cyanoborohydride / tetrahydrofuran / 2.58 h / 50 °C
2.1: methanol; sodium hydroxide / 4 h / 25 °C
3.1: sodium hydride / tetrahydrofuran; hexanes; N,N-dimethyl-formamide / 0.5 h / 25 °C
3.2: 48 h / 25 °C / light protection
4.1: tert.-butylhydroperoxide; selenium(IV) oxide / decane; dichloromethane / 4 h / 0 °C
5.1: Dess-Martin periodane / dichloromethane / 2 h / 25 °C
6.1: aluminum (III) chloride / tetrahydrofuran; diethyl ether / 0.17 h / -30 °C
6.2: 0.33 h / -30 °C
7.1: 1,2-dimethoxyethane; potassium hydride / hexanes / 1 h / Reflux
7.2: -20 - -10 °C
8.1: ozone / dichloromethane / -78 °C
8.2: -78 - 20 °C
9.1: n-butyllithium / hexanes; diethyl ether / 25 °C
9.2: -78 - 25 °C
10.1: diisobutylaluminium hydride / diethyl ether / 3 h / -78 °C
10.2: -78 - 20 °C
11.1: 4-methyl-morpholine; tert.-butylhydroperoxide; osmium(VIII) oxide / tetrahydrofuran; water; tert-butyl alcohol / 25 °C
With
4-methyl-morpholine; methanol; tert.-butylhydroperoxide; selenium(IV) oxide; aluminum (III) chloride; osmium(VIII) oxide; n-butyllithium; 1,2-dimethoxyethane; boron trifluoride diethyl etherate; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium cyanoborohydride; Dess-Martin periodane; ozone; sodium hydroxide;
In
tetrahydrofuran; hexanes; diethyl ether; decane; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
3.1: Williamson synthesis / 3.2: Williamson synthesis / 7.1: oxy-Cope rearrangement;
DOI:10.1002/chem.201100503