1: With n-butyllithium in tetrahydrofuran Wittig reaction; 2: With hydrogen; palladium dihydroxide in methanol

1: AlCl3 / 1,2-dichloro-ethane / 4 h 2: hydrazine hydrate, potassium hydroxide / ethane-1,2-diol / 20 - 160 °C 3: NaBH4, BF3*OEt2 View Scheme

1.1: n-BuLi / tetrahydrofuran 1.2: 57 percent / n-BuLi / tetrahydrofuran; dimethylformamide 2.1: n-BuLi / tetrahydrofuran 2.2: 81 percent / H2 / Pd(OH)2/C / methanol View Scheme

1.1: PCC; NaOAc; molecular sieves / CH2Cl2 1.2: 76 percent / Et3N / CH2Cl2 2.1: 87 percent / NaBH4 / CeCl3 / methanol 3.1: 83 percent / (-)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH2Cl2 / -20 °C 4.1: DBU / CH2Cl2 / 1.5 h / 0 °C 4.2: Et2AlCl / CH2Cl2 / 0 - 20 °C 5.1: 1H-tetrazole / CH2Cl2; acetonitrile 5.2: t-BuOOH / 20 °C 6.1: aq. HCl / tetrahydrofuran / 20 °C View Scheme

1.1: PCC; NaOAc; molecular sieves / CH2Cl2 1.2: 76 percent / Et3N / CH2Cl2 2.1: 87 percent / NaBH4 / CeCl3 / methanol 3.1: 83 percent / (+)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH2Cl2 / -20 °C 4.1: DBU / CH2Cl2 / 1.5 h / 0 °C 4.2: 74 percent / Et2AlCl / CH2Cl2 / 0 - 20 °C 5.1: 1H-tetrazole / CH2Cl2; acetonitrile / 6 h 5.2: 78 percent / t-BuOOH / 20 °C 6.1: 81 percent / aq. HCl / tetrahydrofuran / 20 °C View Scheme