Multi-step reaction with 10 steps
1.1: 97 percent / imidazole / dimethylformamide / 20 °C
2.1: OsO4; NMO / tetrahydrofuran; H2O / 20 °C
2.2: NaIO4 / tetrahydrofuran; H2O
2.3: 75 percent / NiCl2; CrCl2 / dimethylsulfoxide / 20 °C
3.1: 91 percent / Dess-Martin periodinane
4.1: 99 percent / BH3*THF; (S)-Corey-Bakshi-Shibata oxazaborolidine reagent / tetrahydrofuran / -40 °C
5.1: 85 percent / TBAF / tetrahydrofuran / 20 °C
6.1: PdCl2(CH3CN)2 / tetrahydrofuran / 1 h / -5 °C
6.2: 60 percent / benzoquinone / tetrahydrofuran / 48 h / 20 °C
7.1: 92 percent / K2CO3 / methanol / 20 °C
8.1: 91 percent / Dess-Martin periodinane
9.1: 94 percent / PPh3 / CH2Cl2 / 0 °C
10.1: n-BuLi / tetrahydrofuran / -78 °C
10.2: 83 percent / tetrahydrofuran / -78 - 0 °C
With
1H-imidazole; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; borane-THF; (S)-Corey-Bakshi-Shibata oxazaborolidine reagent; tetrabutyl ammonium fluoride; potassium carbonate; Dess-Martin periodane; triphenylphosphine;
dichloro bis(acetonitrile) palladium(II);
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
3.1: Dess-Martin oxidation / 8.1: Dess-Martin oxidation;
DOI:10.1002/anie.200500029