title: Synthetic approaches toward total synthesis of 12 beta-methyl- and 12-methylene-19-norpregnanes.
abstract: 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.
authors.affiliation: Organon International B.V., Scientific Development Group, Oss, The Netherlands.
authors.forename: A I
authors.initials: AI
authors.lastname: Broess
authors.forename: N P
authors.initials: NP
authors.lastname: van Vliet
authors.forename: M B
authors.initials: MB
authors.lastname: Groen
authors.forename: H
authors.initials: H
authors.lastname: Hamersma
mesh_terms: D017135:Desogestrel / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008745:Methylation; D015394:Molecular Structure; D011278:Pregnanes / Q000138:chemical synthesis* / Q000737:chemistry; D013329:Structure-Activity Relationship
chemical_list: D011278:Pregnanes; C044815:etonogestrel; D017135:Desogestrel