Steroids and related products. LIII. The synthesis of 11-oxa steroids. V. The synthesis of 17-ethynyl-11-oxatestosterone.
The synthesis of 17-ethynyl-11-oxatestosterone, both from 11-oxa-5 alpha-pregnane-3,20-dione and, via a 3,17-dioxygenated 9-oxo 9,12-seco 11-nor 5 alpha-androstane-12-oic ester, from 3 beta-acetoxy-17-hydroxy-5 alpha-pregnan-12-one--two products available from hecogenin--is reported. The new hormone analogue shows significant progestational activity in the Clauberg test and relatively weak activity in a post-coital antifertility assay.
D045167:Progesterone Congeners / Q000138:chemical synthesis*; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis*; D013739:Testosterone / Q000031:analogs & derivatives* / Q000138:chemical synthesis
D045167:Progesterone Congeners; D013260:Steroids, Heterocyclic; C053206:17-ethinyl-11-oxa-testosterone; D013739:Testosterone