Acta Chimica Sinica ›› 1989, Vol. 47 ›› Issue (1): 89-92. Previous Articles     Next Articles

Original Articles

17α-羟基-16β-甲基-5,9(11)-孕甾二烯-3,20-二缩酮的D环高碳化

倪元;夏克敏;彭贵章   

  1. 中国科学院上海有机化学研究所;上海第十二制药厂
  • 出版日期:1989-01-15 发布日期:1989-01-15

D-Homoannulation of 17α-hydroxy-16β -methyl-5,9(11)-pregnadiene-3,20-dione-bis(diethylene ketal)

NI YUAN;XIA KEMING;PENG GUIZHANG   

  • Online:1989-01-15 Published:1989-01-15

17a-Hydroxy-16b-methyl-5,9(11)-pregnadiene-3, 20-dione-bis(diethylene ketal) (I) on treatment with 70% acetic acid was hydrolyzed to the parent 3,20-dione (II) in 88% yield, while compound I or II on treatment with 98% acetic acid was rearranged to 17a-hydroxy-16b,17b-dimethyl-D-homo-4,9(11)-androstanediene-3,17a- dione (III) in 68 or 89% yields, resp. I and II reacted with 70% acetic acid containing CaCl2 to give 16b,17ab-dimethyl-D-homo-4,9(11),15-androstrien-3,17-dione (IV) in 90% yield. The yield of compound IV is dependent on the concentration of CaCl2 and the time of reaction.

Key words: REACTION MECHANISM, STEROIDS, REARRANGEMENT REACTION, ACETIC ACID, PREGNENEDIONE

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