Multi-step reaction with 7 steps
1: 89 percent / PPh3 / tetrahydrofuran; H2O / 18 h / 60 °C
2: 1) Me3SiCl, Et3N, 2) t-BuMgCl / 1) Et2O, 0 deg C, 1 h, 2) Et2O, room temp., 18 h
3: 99 percent / H2 / 10 percent Pd/C / tetrahydrofuran / Ambient temperature
4: 72 percent / dimethylformamide; acetic acid / 40 - 50 °C
5: 1) NaOMe / 1) MeOH, -30 deg C, 15 min, 2) MeOH, a) -30 deg C, 30 min, b) 10 deg C, 10 min
6: 90 percent / 2,6-lutidine / tetrahydrofuran / 2 h / -78 °C
7: 1) ozone, 2) Me2S / 1) CH2Cl2, -78 deg C, 2) 0 deg C, 15 min
With
2,6-dimethylpyridine; chloro-trimethyl-silane; dimethylsulfide; tert-butylmagnesium chloride; hydrogen; sodium methylate; ozone; triethylamine; triphenylphosphine;
palladium on activated charcoal;
In
tetrahydrofuran; water; acetic acid; N,N-dimethyl-formamide;
DOI:10.1021/jo00304a024