Scheme 3.
Preparation of ABC-tricycle 2. Reagents and conditions: a) Bu2BOTf, iPr2NEt, THF, −78 °C to −20 °C, 98 %, 2:1 d.r.; b) DMP, NaHCO3, CH2Cl2, 83 %; c) TESCl, imid, DMF, RT, 15: 65 %, 11-epi-15: 29 %; d) SmI2, 65 °C, 2 h, 51 %; e) PPTS, MeOH, CH2Cl2, RT, 88 %; f) PCC, NaOAc, SiO2, CH2Cl2, 2: 81 %, 18: 11 %. DMF=N,N-dimethylformamide, DMP=Dess–Martin periodinane, PCC=pyridinium chlorochromate, PPTS=pyridinium para-toluenesulfonate, TES= triethylsilyl.