1.1: 72 percent / BF3*OEt2 / acetic anhydride / 3 h / 0 °C 2.1: 85 percent / allyl methyl carbonate; DPPE; Bu3SnOMe / Pd(OAc)2 / acetonitrile / 5 h / 80 °C 3.1: 94 percent / DIBAL / tetrahydrofuran; hexane / 1.5 h / -78 °C 4.1: 76 percent / PCC; Celite / CH2Cl2 / 2 h 5.1: 85 percent / imidazole / dimethylformamide 6.1: 73 percent / I2; pyridine / CCl4 7.1: n-BuLi / diethyl ether; hexane 7.2: CuCN / diethyl ether; hexane 7.3: 62 percent / BF3*Et2O / diethyl ether; hexane / -78 °C 8.1: EtMgBr / tetrahydrofuran / 0.17 h / 0 °C 8.2: 66 percent / tetrahydrofuran / 2 h / 0 °C 9.1: Ni(acac)2 / tetrahydrofuran / 0.17 h / 0 °C 9.2: 93 percent / tetrahydrofuran 10.1: 73 percent / NaSEt / dimethylformamide / 12 h / 140 °C 11.1: 84 percent / ZnBr2; MgSO4 / CH2Cl2 / 12 h 12.1: 68 percent / NaSEt / dimethylformamide / 8 h / 120 °C View Scheme

Et2AlCl2 in dichloromethane T=25°C; 3 h;