1: ammonium chloride / methanol / 48 h / Reflux 2: palladium on carbon; hydrogen / ethanol / 4.5 h / 20 °C / 760.05 Torr 3: sulfuric acid; water / dichloromethane / 15 h / 20 °C View Scheme

1.1: n-BuLi / tetrahydrofuran 1.2: 81 percent / H2 / Pd(OH)2/C / methanol 2.1: PCC; NaOAc; molecular sieves / CH2Cl2 2.2: 76 percent / Et3N / CH2Cl2 3.1: 87 percent / NaBH4 / CeCl3 / methanol 4.1: 83 percent / (-)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH2Cl2 / -20 °C 5.1: DBU / CH2Cl2 / 1.5 h / 0 °C 5.2: Et2AlCl / CH2Cl2 / 0 - 20 °C 6.1: 1H-tetrazole / CH2Cl2; acetonitrile 6.2: t-BuOOH / 20 °C 7.1: aq. HCl / tetrahydrofuran / 20 °C View Scheme

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

1.1: n-BuLi / tetrahydrofuran 1.2: 81 percent / H2 / Pd(OH)2/C / methanol 2.1: PCC; NaOAc; molecular sieves / CH2Cl2 2.2: 76 percent / Et3N / CH2Cl2 3.1: 87 percent / NaBH4 / CeCl3 / methanol 4.1: 83 percent / (+)-DIPT; cumene hydroperoxide; MS / Ti(OPr-i)4 / CH2Cl2 / -20 °C 5.1: DBU / CH2Cl2 / 1.5 h / 0 °C 5.2: 74 percent / Et2AlCl / CH2Cl2 / 0 - 20 °C 6.1: 1H-tetrazole / CH2Cl2; acetonitrile / 6 h 6.2: 78 percent / t-BuOOH / 20 °C 7.1: 81 percent / aq. HCl / tetrahydrofuran / 20 °C View Scheme