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Preparation of tritium‐labeled compounds. V. A group of steroids by catalytic reduction of unsaturated precursors with tritium gas
Author(s) -
Thomas Richard C.,
Ikeda George J.,
Campbell J. Allan,
Harpootlian Harry
Publication year - 1975
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590110115
Subject(s) - chemistry , tritium , diene , acetal , methylene , catalysis , medicinal chemistry , pregnane , nuclear chemistry , organic chemistry , natural rubber , physics , nuclear physics
A group of Δ 4 ‐3‐keto steroids was prepared by catalytic reduction of suitable conjugated diene‐3‐keto precursors with tritium gas. Thus, 11α‐hydroxy‐4‐pregnene‐3,20‐dione‐7‐ 3 H (I), 20α‐hydroxy‐4‐pregnen‐3‐one‐7‐ 3 H (II), 6α‐methyl‐4‐pregnene‐3,11,20‐trione‐7‐ 3 H (III), 17α‐hydroxy‐6α‐methyl‐4‐pregnene‐3,20‐dione‐7‐ 3 H, acetate (IV), and 17α‐hydroxy‐6‐methyl‐ 3 H 3 ‐16‐methylenepregna‐4, 6‐diene‐3,20‐dione, acetate (V) were prepared from 11α‐hydroxypregna‐4,6‐diene‐3,20‐dione (VI), 20α‐hydroxypregna‐4,6‐dien‐3‐one (VII), 6‐methylpregna‐4,6‐diene‐3,11,20‐trione (VIII), 17α‐hydroxy‐6‐methylpregna‐4,6‐diene‐3,20‐dione, acetate (IX), and 17α‐hydroxy‐6‐dibromomethylene‐16‐methylene‐4‐pregnene‐3,20‐dione, acetate (X), respectively. In addition, 3α‐hydroxy‐5β‐pregnane‐11,20‐dione‐7‐ 3 H, cyclic 20‐(trimethylene acetal) (XI) was prepared from I via 11α‐hydroxy‐5β‐pregnane‐3,20‐dione‐7‐ 3 H (XII), 5β‐pregnane‐3,11,20‐trione‐7‐ 3 H (XIII) and 3α‐pregnane‐11,20‐dione‐7‐ 3 H (XIV).