Fig. 25.
Reagents: a 1. Me2SO4, K2CO3, 80 °C. 2. S-BuLi, DMF, − 78 °C to rt. 3. NaOH, Me2CO, 60 °C; b 1. NaBH4. 2. Savinase 12 T, vinyl butyrate. 3. NaOH, H2O, EtOH, reflax; c oxazaborolidine, BH3THF, toluene, − 78 °C, d 1. DCC, DMAP. 2. KHMDS, − 78 °C. 3. TMSCL, py, − 78 °C to rt; e MeLi and f 1. Grubb’s 2nd gen. 2. Ph3P=CH2, 75 °C. 3. MeMgI, 160 °C