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...

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Veröffentlicht in:	Steroids 1986-06, Vol.47 (6), p.381-399
Hauptverfasser:	ENGEL, C. R, MUKHERJEE, D, ROY CHOWDHURY, M. N, SALVI, V. S
Format:	Artikel
Sprache:	eng
Schlagworte:	Alicyclic compounds, terpenoids, prostaglandins, steroids Chemistry Exact sciences and technology Organic chemistry Preparations and properties Progesterone Congeners - chemical synthesis Steroids Steroids, Heterocyclic - chemical synthesis Testosterone - analogs & derivatives Testosterone - chemical synthesis
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Zusammenfassung:	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.
ISSN:	0039-128X 1878-5867
DOI:	10.1016/0039-128X(86)90054-1