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The synthesis of 6-chloro-17-hydroxypregna-4,6-diene-3,20-dione-4−14c acetate (chlormadinone-4−14C acetate)

✍ Scribed by K. H. Palmer; R. W. Handy; M. E. Wall

Publisher
John Wiley and Sons
Year
1971
Tongue
French
Weight
329 KB
Volume
7
Category
Article
ISSN
0022-2135

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✦ Synopsis

Chlormadinone-4-14C acetate ( V ) was synthesized from 17%hydroxyprogesterone-4-14C ( I ) by dehydrogenation to the 4,6-diene ( I I ) which was converted to the 6-chloro-4,6-diene ( I V ) via the intermediate 6a,7aor-epoxy compound ( I I I ) , Acetylation of ( I V ) gave chIormadinone-4-14C acetate in 13 overall yield. A secondary reaction product, 6-chloro-androsta-4,6-diene-3,1 7-dione-4-14C was isolated and identified. * Supported by Contract No. PH-43-65-1057, Pharmacology-Toxicology Program o f ** The present paper is the IVth in a series on metabolism of antifertility steroids,

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