Broess A I, van Vliet N P, Groen M B, Hamersma H
Organon International B.V., Scientific Development Group, Oss, The Netherlands.
Steroids. 1992 Nov;57(11):514-21. doi: 10.1016/0039-128x(92)90020-a.
The effect of a substituent in the 12-position of progestagens was studied. To this end, various approaches toward the preparation of 12 beta-alkyl- and 12-alkylidenenorpregnanes were investigated. Eventually, the desired compounds 17 beta-hydroxy-12 beta-methyl-18a-homo-19-nor-17 alpha-pregn-4-en-20-yn-3-one (37) and 17 beta-hydroxy-12-methylene-18a-homo-19-nor-17 alpha-pregn-4-en-20-yn- 3-one (38) were obtained in racemic form by total synthesis; they were shown to lack progestagenic activity.
研究了孕激素12位取代基的作用。为此，研究了各种制备12β-烷基-和12-亚烷基去甲孕烷的方法。最终，通过全合成以消旋形式获得了所需化合物17β-羟基-12β-甲基-18a-高-19-去甲-17α-孕-4-烯-20-炔-3-酮（37）和17β-羟基-12-亚甲基-18a-高-19-去甲-17α-孕-4-烯-20-炔-3-酮（38）；结果表明它们缺乏孕激素活性。
