1: 73 percent / various solvent(s) / 0.08 h / Heating 2: 1) Li, liquid NH3 / 1) THF, -78 deg C, 45 min, 2) -78 deg C, 30 min 3: 1) Hg(OCOCF3)2, 2) aq. HCl / 1) CH3NO2, rt, 42 h, 2) rt, 1 h 4: 86 percent / aq. KOH / methanol / 1.5 h / Ambient temperature 5: 54 percent / D-camphor-10-sulfonic acid / benzene / 3 h / Heating 6: 80 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C 7: 83 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 8: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 9: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 10: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

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

1: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 2: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 3: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

1: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 2: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

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

1: 83 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 2: 1) n-butyllithium / 1) THF, hexane, -78 deg C, 4 min, 2) -78 deg C, 30 min 3: 72 percent / DMSO, oxalyl chloride, NEt3 / 1) CH2Cl2, -78 deg C, 1 h, 2) 0 deg C, 1 h 4: 75 percent / aq. HCl / methanol / 96 h / Ambient temperature View Scheme

sodium hydroxide; real cortex homogenate of guinea pig; nicotinamide adenine dinucleotide in dichloromethane T=37°C; Oxidation; 1 h; Enzyme kinetics; Further Variations:Reagents;

T=37°C; 2 h; 17,20-lyase, metyrapone, NAD+, malic acid;

silica gel in solid 96 h; Irradiation;

in ethanol culture of Cunningamella urvilaria lunata; also other cultures: C. blakesleeana, Th. hyalospora or Th. hiegemella orchidis were used; different times and temperatures of their preparation before reaction; Product distribution;