Multi-step reaction with 16 steps
1.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere
2.1: 1H-imidazole / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere
3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 1 h / 20 °C / pH 7
3.2: 1 h / 20 °C / Inert atmosphere
4.1: toluene / 16 h / 112 °C / Inert atmosphere; Sealed tube; High pressure
5.1: sodium hydride / 1,2-dimethoxyethane / 1 h / 20 °C / Inert atmosphere
5.2: 3 h / Inert atmosphere; Reflux
6.1: diisobutylaluminium hydride / tetrahydrofuran; toluene / 1.5 h / -78 °C / Inert atmosphere
7.1: L-(+)-diisopropyl tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane; decane / -78 - -50 °C / Molecular sieve; Inert atmosphere
8.1: sodium bis(2-methoxyethoxy)aluminium dihydride / tetrahydrofuran; toluene / 2.5 h / 0 °C / Inert atmosphere
9.1: pyridine / dichloromethane / 3 h / Inert atmosphere
10.1: camphor-10-sulfonic acid / dichloromethane; ethanol / 1.5 h / 0 °C / Inert atmosphere
11.1: pyridine / dichloromethane / 1.5 h / Inert atmosphere
12.1: ammonium hydroxide; water / dichloromethane; ethanol / 1 h / 20 °C
13.1: triethylamine / dichloromethane / 0.33 h / -78 °C / Inert atmosphere
14.1: water; acetic acid / tetrahydrofuran / 1.5 h / 0 °C
15.1: Dess-Martin periodane; sodium hydrogencarbonate / dichloromethane / 1 h / 20 °C / Inert atmosphere
16.1: lithium diisopropyl amide / tetrahydrofuran; diethyl ether / 0.33 h / -78 °C / Inert atmosphere
16.2: 0.33 h / -78 °C / Inert atmosphere
With
pyridine; 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; ammonium hydroxide; L-(+)-diisopropyl tartrate; camphor-10-sulfonic acid; 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; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene;
3.2: |Dess-Martin Oxidation / 4.1: |Wittig Olefination / 5.1: |Horner-Wadsworth-Emmons Olefination / 5.2: |Horner-Wadsworth-Emmons Olefination / 7.1: |Sharpless Asymmetric Epoxidation / 15.1: |Dess-Martin Oxidation;
DOI:10.1021/jo3026077