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Synthesis of labelled [ 13 C 6 ]testosterone and [ 13 C 5 ]19‐nortestosterone
Author(s) -
Joubert Cécile,
Beney Chantal,
Marsura Alain,
LuuDuc Cuong
Publication year - 1995
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580360806
Subject(s) - chemistry , radiochemistry , carbon 14 , testosterone (patch) , nuclear physics , physics , endocrinology , medicine
Abstract The condensation of ethyl acetoacetate‐ 13 C 4 and ethyl bromoacetate‐ 13 C 2 afforded, in seven steps, (1,2,3,4,5‐ 13 C 5 ) 5‐(diethylphosphono)‐2‐pentanone ethylene ketal 9 . The reaction of this labelled compound with 7‐[[(1,1‐dimethylethyl)‐dimethylsilyl]oxy]‐1,6,6a,7,8,9,9a, 9b‐octahydro‐6a‐methyl‐[6aS‐(6aa,7a,9aβ,9ba)] cyclopental[f][1]benzopyran‐3 (2H)‐one 13 gave the benzindenone 14 which was converted to (1,2,3,4,10,19‐ 13 C 6 )testosterone 17 then, into (1,2,3,4,10‐ 13 C 5 ) 19‐nortestosterone 18 by a reductive alkylation method.