Reduction of 17β-acetoxy-17α-ethynyl-3-methoxyestra-1,3,5(10)-triene with metals in liquid ammonia
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In the reduction of mestranol acetate with metals in liquid ammonia, as well as the reduction of ring A and the splitting out of the acetoxy group, the addition of hydrogen to C17 takes place and the main products are the 17-vinyl and 17-ethyl derivatives (III) and (VII), respectively. Under conditions favoring the saponification of the acetate, the reduction product is the 17-ethylidene derivative (VIII).
KeywordsEnol Liquid Ammonia Hydrofuran Metallic Sodium Acetoxy Group
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