lipase from Candida cylindracea; octanol in water; acetonitrile T=37°C; 144 h;

hydrogenchloride in methanol 96 h; Ambient temperature;

1: 78 percent / CHCl3; diethyl ether / 1 h / 0 °C 2: 98 percent / D-Camphor-10-sulfonic acid / benzene / 12 h / Heating 3: 84 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C 4: 83 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 5: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 6: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 7: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

1: 98 percent / D-Camphor-10-sulfonic acid / benzene / 12 h / Heating 2: 84 percent / LiAlH4 / tetrahydrofuran / 0.25 h / 0 °C 3: 83 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 4: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 5: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 6: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

1: 1) Li, liquid NH3 / 1) THF, -78 deg C, 45 min, 2) -78 deg C, 30 min 2: 1) Hg(OCOCF3)2, 2) aq. HCl / 1) CH3NO2, rt, 42 h, 2) rt, 1 h 3: 86 percent / aq. KOH / methanol / 1.5 h / Ambient temperature 4: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating 5: 80 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 6: 83 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 7: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 8: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 9: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

1: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating 2: 80 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 3: 83 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 4: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 5: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 6: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

1: 86 percent / aq. KOH / methanol / 1.5 h / Ambient temperature 2: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating 3: 80 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 4: 83 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 5: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 6: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 7: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

1: 1) Hg(OCOCF3)2, 2) aq. HCl / 1) CH3NO2, rt, 42 h, 2) rt, 1 h 2: 86 percent / aq. KOH / methanol / 1.5 h / Ambient temperature 3: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating 4: 80 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 5: 83 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 6: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 7: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 8: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

1: 95 percent / pyridinium dichromate / CH2Cl2 / 5 h / Ambient temperature 2: 98 percent / aq. HCl / methanol / 2 h / Ambient temperature 3: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating 4: 80 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 5: 83 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 6: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 7: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 8: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

1: 98 percent / aq. HCl / methanol / 2 h / Ambient temperature 2: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating 3: 80 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 4: 83 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 5: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 6: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 7: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme