Steroids and related products. XLI. (1) the synthesis of 11-oxa steroids. III. (2) 17-acetoxy-11-oxaprogesterone (3).
The synthesis of 17-acetoxy-11-oxaprogesterone, the 11-oxa analogue of the orally active progestational and anti-fertility agent 17-acetoxyprogesterone, is described. An intermediate in the synthesis of 11-oxaprogesterone, 11-oxa-5alpha-pregnane-3,20-dione, available from hecogenin, was used as starting material and the 17-hydroxy function was introduced by a modified Barton oxidation. The new hormone analogue shows only extremely weak progestational activity in the oral Clauberg assay.
D003276:Contraceptives, Oral / Q000494:pharmacology; D006908:Hydroxyprogesterones / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000502:physiology; D008722:Methods; D013260:Steroids, Heterocyclic / Q000138:chemical synthesis* / Q000494:pharmacology
D003276:Contraceptives, Oral; D006908:Hydroxyprogesterones; D013260:Steroids, Heterocyclic; C010668:17-acetoxy-11-oxaprogesterone