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