Multi-step reaction with 11 steps
1.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C / pH 7
2.2: 1 h / 20 °C / Inert atmosphere
3.1: toluene / 16 h / 112 °C / Inert atmosphere; Sealed tube; High pressure
4.1: sodium hydride / 1,2-dimethoxyethane / 1 h / 20 °C / Inert atmosphere
4.2: 3 h / Inert atmosphere; Reflux
5.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1.5 h / -78 °C / Inert atmosphere
6.1: L-(+)-diisopropyl tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane; decane / -78 - -50 °C / Molecular sieve; Inert atmosphere
7.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / 0 °C / Inert atmosphere
8.1: triethylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
9.1: water; acetic acid / tetrahydrofuran / 1.5 h / 0 °C
10.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
11.1: lithium diisopropyl amide / tetrahydrofuran; diethyl ether / 0.25 h / -78 °C / Inert atmosphere
11.2: 0.5 h / -78 °C / Inert atmosphere
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; L-(+)-diisopropyl tartrate; water; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; Dess-Martin periodane; acetic acid; triethylamine; sodium bis(2-methoxyethoxy)aluminium dihydride; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide;
In
tetrahydrofuran; 1,2-dimethoxyethane; diethyl ether; decane; dichloromethane; N,N-dimethyl-formamide; toluene;
2.2: |Dess-Martin Oxidation / 3.1: |Wittig Olefination / 4.1: |Horner-Wadsworth-Emmons Olefination / 4.2: |Horner-Wadsworth-Emmons Olefination / 6.1: |Sharpless Asymmetric Epoxidation / 10.1: |Dess-Martin Oxidation;
DOI:10.1021/jo3026077