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化学学报
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化学学报 ›› 1975, Vol. 33 ›› Issue (2): 139-147. 上一篇    下一篇

论文

口服避孕药三烯炔诺酮和dl-18-甲基三烯炔诺酮的合成

甾族激素组1, 上海第九制药厂2   

  1. 1. 中国科学院上海有机化学研究所;
    2. 上海第九制药厂
  • 投稿日期:1974-09-09 发布日期:2013-06-03

SYNTHESES OF THE ORAL CONTRACEPTIVES NORGESTRIENONE AND dl-18-METHYL-NORGESTRIENONE

STEROID HORMONE GROUP1, SHANGHAI No.9 PHARMACEUTICAL WORKS2   

  1. 1. Shanghai Institute of Organiv Chemistry, Academia Sinica;
    2. SHANGHAI No.9 PHARMACEUTICAL WORKS
  • Received:1974-09-09 Published:2013-06-03

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三烯炔诺酮(17α-乙炔基-17β-羟基雌甾-4,9,11-三烯-3-酮,Ⅰa)具有较异炔诺酮(Ⅱ)更强的抗排卵作用,与炔雌醚(Ⅲ)合用乃是一种常用的口服避孕药.本品若在房事前后,单独服用低剂量,也具有抑制生育的作用.18-甲基三烯炔诺酮(18-甲基-17α-乙炔基-17β-羟基性甾-4,9,11-三烯-3-酮,Ⅰb)是一种抗着床的口服避孕药,每星期只需服用一次.此药既不抑制排卵,也不产生因每月服用22天含有炔雌醚的口服抗排卵避孕药而引起的副作用.三烯炔诺酮(Ⅰa)系用半合成方法合成,即以Ⅹ为原料,经Ⅺ→Ⅸa→Ⅶa→Ⅳa→Ⅻa→ⅫⅠa→ⅪⅤa而得Ⅰa,或不经Ⅻa及ⅫⅠa,即将Ⅳa经选择乙炔化而直接得ⅪⅤa.dl-18-甲基三烯炔诺酮(Ⅰb)用全合成方法合成,以Ⅷb为原料,采用与合成三烯炔诺酮相似的合成路线,经Ⅸb→Ⅶb→Ⅳb→Ⅻb→ⅫⅠb→ⅪⅤb而得Ⅰb.或不经Ⅶb及Ⅳb,即将Ⅸb与无水甲醇、氯化氢气体作用而直接得Ⅻb.

Norgestrienone(Ⅰa)was prepared by partial synthesis either from X through the following sequence of reactions:ⅩⅠ→Ⅸ→Ⅶa→Ⅳa→Ⅶa→Ⅷa→ⅩⅣa→Ⅰa,or directly from Ⅳa to ⅩⅣa by selective ethynylation.dl-18-Methyl-norgestrienone(Ⅰb)was prepared by total synthesis from Ⅷb according to the reaction sequence similar to that of norgestrienone,i.e.,Ⅸb→Ⅶb→Ⅳb,ⅩⅡb→ⅩⅢb→ⅩⅣb→Ⅰb.Furthermore,ⅩⅡb can be obtained directly from ⅠⅩb,by hydrogen ohloride treatment in absolute methanol.