1.1: NaNO2; aq. HCl / tetrahydrofuran / 0 °C 1.2: NaN3 / tetrahydrofuran / 0 - 20 °C 2.1: DIBALH / CH2Cl2 / -78 °C 3.1: NaClO2; 2-methyl-2-butene; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C 4.1: 100 percent / DCC / CH2Cl2 / 20 °C 5.1: 76 percent / n-Bu3P / toluene / 20 °C 6.1: NaH / dimethylformamide / 0 - 20 °C 7.1: n-BuONO; KHMDS / tetrahydrofuran / 0 °C 8.1: Zn; TFA / CH2Cl2 / 20 °C View Scheme

sodium hydroxide in methanol; water T=90°C; 8 h;

1.1: NaNO2; aq. HCl / tetrahydrofuran / 0 °C 1.2: NaN3 / tetrahydrofuran / 0 - 20 °C 2.1: DIBALH / CH2Cl2 / -78 °C 3.1: NaClO2; 2-methyl-2-butene; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 0 - 20 °C 4.1: 100 percent / DCC / CH2Cl2 / 20 °C 5.1: 76 percent / n-Bu3P / toluene / 20 °C 6.1: NaH / dimethylformamide / 0 - 20 °C View Scheme