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Synthesis of labelled [13C6]testosterone and [13C5]19-nortestosterone

✍ Scribed by Cécile Joubert; Chantal Beney; Alain Marsura; Cuong Luu-Duc


Publisher
John Wiley and Sons
Year
1995
Tongue
French
Weight
591 KB
Volume
36
Category
Article
ISSN
0022-2135

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✦ Synopsis


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.


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