## Abstract [__phenyl__‐^13^C~6~]Lachnanthocarpone ([__phenyl__‐^13^C~6~]2,6‐dihydroxy‐9‐phenylphenalen‐1‐one), a hypothetical intermediate in the biosynthesis of various natural phenylphenalenones, was prepared in four steps using [U‐^13^C]bromobenzene to introduce the label. Based on related meth
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
No coin nor oath required. For personal study only.
✦ 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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