1: HClO2; NaH2PO4; DMS / tetrahydrofuran; H2O / 2 h / 20 °C 2: 173.3 g / tetrahydrofuran; methanol View Scheme

1.1: 27.3 g / p-TSA / methanol / 6 h / 20 °C 2.1: n-BuLi / tetrahydrofuran / 4.25 h / -15 - 0 °C 2.2: tetrahydrofuran; CH2Cl2 / -10 °C 3.1: 14.5 g / DDQ / CH2Cl2; H2O / 2 h / 20 °C 4.1: 72 percent / Br2; NaOAc; acetic acid / 8 h / 20 °C 5.1: HClO2; NaH2PO4; DMS / tetrahydrofuran; H2O / 2 h / 20 °C 6.1: 173.3 g / tetrahydrofuran; methanol View Scheme

1: 72 percent / Br2; NaOAc; acetic acid / 8 h / 20 °C 2: HClO2; NaH2PO4; DMS / tetrahydrofuran; H2O / 2 h / 20 °C 3: 173.3 g / tetrahydrofuran; methanol View Scheme

1.1: n-BuLi / tetrahydrofuran / 4.25 h / -15 - 0 °C 1.2: tetrahydrofuran; CH2Cl2 / -10 °C 2.1: 14.5 g / DDQ / CH2Cl2; H2O / 2 h / 20 °C 3.1: 72 percent / Br2; NaOAc; acetic acid / 8 h / 20 °C 4.1: HClO2; NaH2PO4; DMS / tetrahydrofuran; H2O / 2 h / 20 °C 5.1: 173.3 g / tetrahydrofuran; methanol View Scheme

1: 14.5 g / DDQ / CH2Cl2; H2O / 2 h / 20 °C 2: 72 percent / Br2; NaOAc; acetic acid / 8 h / 20 °C 3: HClO2; NaH2PO4; DMS / tetrahydrofuran; H2O / 2 h / 20 °C 4: 173.3 g / tetrahydrofuran; methanol View Scheme

in tetrahydrofuran; methanol