Multi-step reaction with 17 steps
1.1: tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere
1.2: 4.17 h / 25 °C
2.1: 1H-imidazole / 1,2-dichloro-ethane / 0 - 25 °C / Inert atmosphere
3.1: trimethylaluminum; N-ethyl-N,N-diisopropylamine / hexane; dichloromethane / 2 h / -78 - 25 °C / Inert atmosphere
4.1: toluene / 0.25 h / 0 °C
4.2: 0.08 h / 0 °C
4.3: 20 °C
5.1: dichloromethane / 0.17 h / 0 °C / Inert atmosphere
5.2: 2 h / 0 °C / Inert atmosphere
6.1: toluene / 1 h / 50 - 60 °C
7.1: tetrahydrofuran; toluene / 25 °C / Inert atmosphere
8.1: dichloromethane / 0.25 h / 0 °C
8.2: 0 °C
9.1: methanol / 0.5 h
9.2: 2 h / 0 °C
10.1: ozone / ethyl acetate / 0.5 h / 40 °C
10.2: 8 h / 20 °C / Inert atmosphere
10.3: 0.5 h / Inert atmosphere
11.1: bis(4-chlorobenzyl) diazene-1,2-dicarboxylate; triphenylphosphine / dichloromethane / 1.5 h / Inert atmosphere
12.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / -15 - -10 °C / Inert atmosphere
13.1: 1H-imidazole / 1,2-dichloro-ethane / 6 h / 0 - 80 °C / Inert atmosphere
14.1: diisobutylaluminium hydride / dichloromethane / 0.17 h / -78 °C / Inert atmosphere
15.1: borane tert-butylamine / ethanol / 1 h / -78 - 25 °C
15.2: 0 °C
16.1: 2,6-dimethylpyridine / dichloromethane / 4 h / -73 - -60 °C / Inert atmosphere
17.1: sodium hydrogencarbonate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 20 °C
With
1H-imidazole; bis(4-chlorobenzyl) diazene-1,2-dicarboxylate; 2,6-dimethylpyridine; methanol; trimethylaluminum; isopropylmagnesium chloride; diisobutylaluminium hydride; borane tert-butylamine; sodium hydrogencarbonate; ozone; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine;
In
tetrahydrofuran; ethanol; hexane; dichloromethane; ethyl acetate; 1,2-dichloro-ethane; toluene;
4.1: Noyori oxidation / 4.2: Noyori oxidation / 4.3: Noyori oxidation / 5.1: Jacobsen epoxidation / 5.2: Jacobsen epoxidation;
DOI:10.1021/ol2024746