3929
Scheme 2. Reagents and conditions. (a) DIBAL, toluene, −78°C, 1 h, 95%; (b) Ph3P_CHCOOMe, benzene, 23°C, 1 h, 64%;
(c) I2, Ph3P, imidazole, toluene, 23°C, 1 h, 79%; (d) DIBAL, toluene, −78°C, 1 h; (e) DHP, p-TsOH, CH2Cl2, 23°C, 1 h, 90% in
two steps; (f) cycloheptanone N,N-dimethylhydrazone, n-BuLi, THF, 23°C, 2 h; (g) silica gel, CH2Cl2, 23°C, 19 h, 92% in two
steps; (h) conc. HCl, dioxane, 23°C, 5 h, 94%; (i) t-BuOK, t-BuOH, reflux, 3.5 h, 28% for 10a, 43% for 10b; (j) allyl iodide,
KHMDS, THF, 0°C, 3 h, 81% (3:11=7:1); (k) RuCl2(_CHPh)(PCy3)2, toluene, reflux, 20% for 12, 76% for 13; (l) H2, Pd/C,
EtOH, 23°C, 1 h, 55% for 2, 68% for 14
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