1: DMSO, (COCl)2 / CH2Cl2 2: TsOH / benzene 3: H2 / Pd-C / ethyl acetate 4: CrO3, H2SO4 / acetone 5: 2N-HCl / tetrahydrofuran / Ambient temperature 6: (C6H11)2NMgBr / methanol / -55 °C 7: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86) View Scheme

Multi-step reaction with 13 steps 1: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -70 deg C, 30 min, 2) CH2Cl2, -70 to 0 deg C2: 1) NaH / 1) DMF, 45 min, 0 deg C, 2) DMF, THF, 0 to 20 deg C3: 94 percent / hydrogen / 10percent Pd/C / ethyl acetate4: 97 percent / tetrahydrofuran / 3 h / -40 °C5: 1) O3, 2) NaBH4 / 1) CH2Cl2, -78 deg C, 20 min, 2) CH2Cl2, MeOH, -78 deg C, 15 min6: 94 percent / Et3N / toluene / 2 h / 0 °C7: 1N HCl / tetrahydrofuran / 4 h / Ambient temperature8: K2CO3 / methanol; H2O / 1 h9: 91 percent / NaH / dimethylsulfoxide / 1 h / Ambient temperature10: 83 percent / CSA / CH2Cl2 / 0.33 h / 0 °C11: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -70 deg C, 2) CH2Cl2, -70 to 0 deg C12: 28 percent / (Ph3P)3RhCl / acetonitrile / 9 h / 160 °C / sealed tube13: 100 percent / DDQ / CH2Cl2; H2O  

Multi-step reaction with 16 steps 1: LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C2: CSA / acetone / 0.5 h / Ambient temperature3: 96 percent / hydrogen / 10percent Pd/C / ethanol / 3.5 h / Ambient temperature4: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -70 deg C, 30 min, 2) CH2Cl2, -70 to 0 deg C5: 1) NaH / 1) DMF, 45 min, 0 deg C, 2) DMF, THF, 0 to 20 deg C6: 94 percent / hydrogen / 10percent Pd/C / ethyl acetate7: 97 percent / tetrahydrofuran / 3 h / -40 °C8: 1) O3, 2) NaBH4 / 1) CH2Cl2, -78 deg C, 20 min, 2) CH2Cl2, MeOH, -78 deg C, 15 min9: 94 percent / Et3N / toluene / 2 h / 0 °C10: 1N HCl / tetrahydrofuran / 4 h / Ambient temperature11: K2CO3 / methanol; H2O / 1 h12: 91 percent / NaH / dimethylsulfoxide / 1 h / Ambient temperature13: 83 percent / CSA / CH2Cl2 / 0.33 h / 0 °C14: 1) (COCl)2, DMSO, 2) Et3N / 1) CH2Cl2, -70 deg C, 2) CH2Cl2, -70 to 0 deg C15: 28 percent / (Ph3P)3RhCl / acetonitrile / 9 h / 160 °C / sealed tube16: 100 percent / DDQ / CH2Cl2; H2O  

Multi-step reaction with 4 steps 1: 1) DMSO, (COCl)2, 2) Et3N / 1) CH2Cl2, -70 deg C, 2) CH2Cl2, -70 to 0 deg C2: 100 percent / p-TsOH / benzene / 1.5 h / Heating; Dean-Stark apparatus3: 83 percent / hydrogen / 10percent Pd/C / ethyl acetate / 15 h / Ambient temperature4: 82 percent / CrO3, H2SO4 / acetone / 0.67 h / 0 °C  

Multi-step reaction with 6 steps 1: DMSO, (COCl)2 / CH2Cl2 2: TsOH / benzene3: H2 / Pd-C / ethyl acetate4: CrO3, H2SO4 / acetone5: 2N-HCl / tetrahydrofuran / Ambient temperature6: (C6H11)2NMgBr / methanol / -55 °C  

Multi-step reaction with 6 steps 1: DMSO, (COCl)2 / CH2Cl2 2: TsOH / benzene3: H2 / Pd-C / ethyl acetate4: CrO3, H2SO4 / acetone5: 2N-HCl / tetrahydrofuran / Ambient temperature6: 23 percent / (C6H11)2NMgBr / tetrahydrofuran / -55 °C  

Multi-step reaction with 7 steps 1: DMSO, (COCl)2 / CH2Cl2 2: TsOH / benzene3: H2 / Pd-C / ethyl acetate4: CrO3, H2SO4 / acetone5: 2N-HCl / tetrahydrofuran / Ambient temperature6: (C6H11)2NMgBr / methanol / -55 °C7: DDQ / CH2Cl2 / 1.5 h / Ambient temperature; buffer (pH 6.86)