Multi-step reaction with 8 steps
1.1: 87 percent / imidazole / dimethylformamide / 24 h
2.1: 74 percent / N-methylmorpholine oxide / RuCl2(PPh3)3 / acetone / 0.42 h
3.1: 68 percent / LiCl; KI; Ga / tetrahydrofuran / 14 h / 60 °C
4.1: 65 percent / DIBAL / diethyl ether / 3 h / 38 °C
5.1: 50 percent / vanadyl acetylacetonate; TBHP / CH2Cl2; 1,2-dichloro-ethane / 24 h
6.1: t-BuOK / tetrahydrofuran / 0.3 h / 0 °C
6.2: 67 percent / aq. NaHSO4 / tetrahydrofuran / 4 h / 20 °C
7.1: 91 percent / i-Pr2NEt; DMAP / CH2Cl2 / 0.25 h / 0 °C
8.1: 90 percent / Pseudomonas cepacia Lipase / acetone; butan-1-ol; hexane / 35 h
With
1H-imidazole; tert.-butylhydroperoxide; dmap; Pseudomonas cepacia lipase; vanadyl acetylacetonate; potassium tert-butylate; diisobutylaluminium hydride; 4-methylmorpholine N-oxide; (3S,3aS,4S,4aS,6S,8aR,8bR,11S)-6,11-dihydroxy-3-methyl-12-methylene-2-oxo-4a,6-ethano-3,8b-prop-1-enoperhydroindeno[1,2-b]furan-4-carboxylic acid; N-ethyl-N,N-diisopropylamine; potassium iodide; lithium chloride;
tris(triphenylphosphine)ruthenium(II) chloride;
In
tetrahydrofuran; diethyl ether; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetone; butan-1-ol;
DOI:10.1021/ol016915f