Catalytic reduction of 3β‐hydroxyandrost‐4‐ene‐17‐one with tritium. II. The distribution and configuration of label in 3β‐hydroxy‐5β‐androstane‐17‐one1

Yusuf J. Abul‐Hajj

Research output: Contribution to journalArticlepeer-review

Abstract

Catalytic reduction of 3β‐hydroxyandrost‐4‐ene‐17one 1 with tritium gas gave a mixture of 3 β‐hydroxy‐5 β‐androstane‐17‐one (II) and 3β‐hydroxy‐5α‐androsiane‐17‐one (III). Oxidation of compound II followed by alkaline equilibration resulted in 29% loss of label. A 29% loss of tritium was observed after bromination of compound II. Dehydrobromination of 4β‐bromo‐5β‐androstane‐3,17‐dione to androst‐4‐ene‐3,17‐dione resulted in 54% loss of tritium. Chloranil dehydrogenation and alkaline equilibration experiments have shown that the remaining radioactivity was at C‐6. Thus the distribution and configuration of label was found to be 29% 4β, 54% 5β, 4.7% 6β and 13% 6α.

Original languageEnglish (US)
Pages (from-to)261-268
Number of pages8
JournalJournal of Labelled Compounds
Volume7
Issue number3
DOIs
StatePublished - Jan 1 1971

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