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A new method for labelling 11β-hydroxy steroids: Synthesis of 18-2H-corticosteroids

✍ Scribed by Michael J. Green; Ho-Jane Shue; Peter Bartner; James B. Morton; Richard E. Youngstrom; Jerrold Meinwald

Book ID: 102373740
Publisher: John Wiley and Sons
Year: 1980
Tongue: French
Weight: 314 KB
Volume: 17
Category: Article
ISSN: 0022-2135
DOI: 10.1002/jlcr.2580170617

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✦ Synopsis

Abstract

A new method for labelling 11β‐hydroxy steroids is described. The procedure involves specifically placing the label on the angular C~13~ methyl group via the photolysis of the 11β‐nitrite ester (Barton reaction) and reaction of the resulting C~18~ radical with PhS‐^2^H in situ. Incorporations of ^2^H were 30‐40% for 9α‐H, 12‐21% for 9α‐F and <5% for 9α‐Cl corticosteroids. The extent of labelling was measured by mass spectrometry and the position of labelling was confirmed as C~18~ for two compounds by dmr, cmr and pmr spectroscopy.

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