Multi-step reaction with 14 steps
1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -78 °C / Inert atmosphere
2.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere
3.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C / pH 7
4.2: 1 h / 20 °C / Inert atmosphere
5.1: toluene / 16 h / 112 °C / Inert atmosphere; Sealed tube; High pressure
6.1: sodium hydride / 1,2-dimethoxyethane / 1 h / 20 °C / Inert atmosphere
6.2: 3 h / Inert atmosphere; Reflux
7.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1.5 h / -78 °C / Inert atmosphere
8.1: L-(+)-diisopropyl tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane; decane / -78 - -50 °C / Molecular sieve; Inert atmosphere
9.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / 0 °C / Inert atmosphere
10.1: triethylamine / dichloromethane / 0.5 h / -78 °C / Inert atmosphere
11.1: water; acetic acid / tetrahydrofuran / 1.5 h / 0 °C
12.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 0.5 h / 20 °C / Inert atmosphere
13.1: lithium diisopropyl amide / tetrahydrofuran / 0.25 h / -78 °C / Inert atmosphere
13.2: 0.08 h / -78 °C / Inert atmosphere
13.3: -78 °C / Inert atmosphere
14.1: dmap / dichloromethane / 0.17 h
With
1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; 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; decane; dichloromethane; N,N-dimethyl-formamide; toluene;
4.2: |Dess-Martin Oxidation / 5.1: |Wittig Olefination / 6.1: |Horner-Wadsworth-Emmons Olefination / 6.2: |Horner-Wadsworth-Emmons Olefination / 8.1: |Sharpless Asymmetric Epoxidation / 12.1: |Dess-Martin Oxidation;
DOI:10.1021/jo3026077