Oxygen → (8R,9S,10R,13S,14R)-14-hydroxy-10,13-dimethyl-2,7,8,9,11,12,15,16-octahydro-1H-cyclopenta[a]phenanthrene-3,6,17-trione
反応式
[OH:1][C@H:2]1[C:19]2[C@:14]([CH3:21])([CH2:15][CH2:16][C:17](=[O:20])[CH:18]=2)[C@@H:13]2[C@H:4]([C@@:5]3([OH:23])[C@@:9]([CH2:11][CH2:12]2)([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]3)[CH2:3]1.O=O>C(Cl)(Cl)Cl>[OH:23][C@:5]12[C@H:4]3[C@@H:13]([C@:14]4([CH3:21])[C:19]([C:2](=[O:1])[CH2:3]3)=[CH:18][C:17](=[O:20])[CH2:16][CH2:15]4)[CH2:12][CH2:11][C@:9]1([CH3:10])[C:8](=[O:22])[CH2:7][CH2:6]2参加物
4
実験手順
6β,14α-dihydroxy-4-androstene-3,17-dione (50 g) thus prepared in the above-mentioned manner was dissolved in 1 liter of chloroform and transferred to a glass sealable vessel; after blowing oxygen therein, the vessel was sealed and allowed to stand for 4 hours under sunlight. Thereafter, the chloroform was removed by evaporation at 40° C. After the evaporation, the resultant residue was analyzed by thin layer chromatography and a spot for 14α-hydroxy-4-androstene-3,6,17-trione only was confirmed. According to this method, 49.2 g of 14α-hydroxy-4-androstene-3,6,17-trione was obtained. The yield was 98.4%.