hydrogenchloride; hydrogen; palladium dihydroxide in ethanol P=3000.2 Torr; 15 h;

2: H2 / Pd(OH)2/C / ethanol View Scheme

2: AcOH 3: O3 4: NaBH4 6: H2 / Pd(OH)2/C / ethanol View Scheme

1: 1.) LDA; 2.) LDA / 2.) -78 deg C 2: Bu3SnH / benzene / 25 °C 4: AcOH 5: O3 6: NaBH4 8: H2 / Pd(OH)2/C / ethanol View Scheme

1: Bu3SnH / benzene / 25 °C 3: AcOH 4: O3 5: NaBH4 7: H2 / Pd(OH)2/C / ethanol View Scheme

1: 93 percent / CF3COOH / CH2Cl2 / 0 °C 2: 1.) LDA; 2.) LDA / 2.) -78 deg C 3: Bu3SnH / benzene / 25 °C 5: AcOH 6: O3 7: NaBH4 9: H2 / Pd(OH)2/C / ethanol View Scheme

1: 92 percent / CH2Cl2 / 25 °C 2: DMSO/(COCl)2, EtN3 3: 93 percent / CF3COOH / CH2Cl2 / 0 °C 4: 1.) LDA; 2.) LDA / 2.) -78 deg C 5: Bu3SnH / benzene / 25 °C 7: AcOH 8: O3 9: NaBH4 11: H2 / Pd(OH)2/C / ethanol View Scheme

1: DMSO/(COCl)2, EtN3 2: 93 percent / CF3COOH / CH2Cl2 / 0 °C 3: 1.) LDA; 2.) LDA / 2.) -78 deg C 4: Bu3SnH / benzene / 25 °C 6: AcOH 7: O3 8: NaBH4 10: H2 / Pd(OH)2/C / ethanol View Scheme

1: LiN(i-Pr)2 / THF, 2h ,-78 deg C 2: diethyl ether 3: Bu3SnH, α,α'-azobis(isobutyronitrile) / benzene / 4 h / Ambient temperature 4: diethyl ether; tetrahydrofuran / 0 deg C to r.t., 16 h 5: aq. CH3CO2H / 6 h / Heating 6: 1.) O3 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C 2.) -78 deg C --> RT, 1h 7: 1.) BuLi / 1.) THF, hexane, -78 deg C, 15 min 2. ) 0 deg C, 2 h 8: 100 percent / H2, 10percent aq. HCl / Pearlman's catalyst / ethanol / 15 h / 3000.2 Torr View Scheme

1: 88 percent / CF3CO2H / CH2Cl2 / 3.5 h / 0 °C 2: LiN(i-Pr)2 / THF, 2h ,-78 deg C 3: diethyl ether 4: Bu3SnH, α,α'-azobis(isobutyronitrile) / benzene / 4 h / Ambient temperature 5: diethyl ether; tetrahydrofuran / 0 deg C to r.t., 16 h 6: aq. CH3CO2H / 6 h / Heating 7: 1.) O3 2.) NaBH4 / 1.) MeOH, CH2Cl2, -78 deg C 2.) -78 deg C --> RT, 1h 8: 1.) BuLi / 1.) THF, hexane, -78 deg C, 15 min 2. ) 0 deg C, 2 h 9: 100 percent / H2, 10percent aq. HCl / Pearlman's catalyst / ethanol / 15 h / 3000.2 Torr View Scheme