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The synthesis of 6‐chloro‐17‐hydroxypregna‐4,6‐diene‐3,20‐dione‐4−14c acetate (chlormadinone‐4−14C acetate)
Palmer, KH., Handy, R., & Wall, M. (1971). The synthesis of 6‐chloro‐17‐hydroxypregna‐4,6‐diene‐3,20‐dione‐4−14c acetate (chlormadinone‐4−14C acetate). Journal of Labelled Compounds and Radiopharmaceuticals, 7(1), 16-22. https://doi.org/10.1002/jlcr.2590070104
Chlormadinone‐4−14C acetate (V) was synthesized from 17α‐hydroxyprogesterone‐4−14C (I) by dehydrogenation to the 4,6‐diene (II) which was converted to the 6‐chloro‐4,6‐diene (IV) via the intermediate 6α,7α‐epoxy compound (III). Acetylation of (IV) gave chlormadinone‐4−14C acetate in 13% overall yield. A secondary reaction product, 6‐chloro‐androsta‐4,6‐diene‐3,17‐dione‐4−14C was isolated and identified.
(The present paper is the IVth in a series on metabolism of antifertility steroids,)