Multi-step reaction with 11 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere
2.1: 1H-imidazole / N,N-dimethyl-formamide / 5 h / 20 °C
3.1: n-butyllithium; N,N,N,N,-tetramethylethylenediamine / tetrahydrofuran / 1 h / 0 °C
3.2: 3 h / 20 °C
4.1: aluminum (III) chloride; sodium iodide / dichloromethane; acetonitrile / 1 h / 0 °C
5.1: (R)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanoltrimethylsilyl ether; benzoic acid / toluene / 88 h / 20 °C
6.1: triethylamine / tetrahydrofuran / 0 - 20 °C
7.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone / 96 h / 20 °C
8.1: toluene / 100 °C
9.1: 5% Pd-BaSO4; hydrogen / ethyl acetate / 1 h / 20 °C / 750.08 Torr
10.1: toluene-4-sulfonic acid / tetrahydrofuran / 24 h / 20 °C
11.1: toluene-4-sulfonic acid / benzene / 16 h / Reflux
With
1H-imidazole; aluminum (III) chloride; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; (R)-(-)-α,α-bis[3,5-bis(trifluoromethyl)phenyl]-2-pyrrolidinemethanoltrimethylsilyl ether; 5% Pd-BaSO4; hydrogen; toluene-4-sulfonic acid; 4-methylmorpholine N-oxide; triethylamine; benzoic acid; sodium iodide;
In
tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetone; toluene; acetonitrile; benzene;
8.1: Wittig reaction;
DOI:10.1002/chem.201102192