1: p-TsOH / CH2Cl2 / 20 °C 2: DIBAL-H / tetrahydrofuran / 0 - 20 °C 3: NCS; Ph3P / CH2Cl2 / 0 - 20 °C 4: n-BuLi; HMPA / tetrahydrofuran / -42 - 20 °C View Scheme

1: p-TsOH / CH2Cl2 / 20 °C 2: DIBAL-H / tetrahydrofuran / 0 - 20 °C 3: NCS; Ph3P / CH2Cl2 / 0 - 20 °C 4: n-BuLi; HMPA / tetrahydrofuran / -42 - 20 °C View Scheme

1: 96 percent / SOCl2 / pyridine / 5 h / 0 °C 2: 92 percent / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 0.5 h / 0 °C 3: 70 percent / MgBr2 / diethyl ether / 12 h / 20 °C 4: 85 percent / NaN3 / dimethylformamide / 12 h / 60 °C 5: 95 percent / CH2Cl2; pyridine / 6 h / 20 °C 6: 90 percent / H2 / 10 percent Pd-C / ethanol / 6 h / 2585.74 Torr View Scheme

1: 96 percent / SOCl2 / pyridine / 5 h / 0 °C 2: 92 percent / NaIO4; RuCl3 / CCl4; acetonitrile; H2O / 0.5 h / 0 °C 3: 70 percent / MgBr2 / diethyl ether / 12 h / 20 °C 4: 85 percent / NaN3 / dimethylformamide / 12 h / 60 °C View Scheme

With  osmium(VIII) oxide; methanesulfonamide; (9-O-indolinylcarbamoyl)dihydroquinidine (DHQD-IND); potassium carbonate; potassium hexacyanoferrate(III) in  water; toluene; tert-butyl alcohol T=0°C;  Yield given. Yields of byproduct given. Title compound not separated from byproducts;   

With  osmium(VIII) oxide; methanesulfonamide; (9-O-indolinylcarbamoyl)dihydroquinidine (DHQD-IND); potassium carbonate; potassium hexacyanoferrate(III) in  water; toluene; tert-butyl alcohol T=0°C;  Yield given. Yields of byproduct given. Title compound not separated from byproducts;