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A new method for labelling 11β‐hydroxy steroids: Synthesis of 18‐ 2 H‐corticosteroids
Author(s) -
Green Michael J.,
Shue HoJane,
Bartner Peter,
Morton James B.,
Youngstrom Richard E.,
Meinwald Jerrold
Publication year - 1980
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.2580170617
Subject(s) - labelling , chemistry , mass spectrometry , radiochemistry , medicinal chemistry , chromatography , biochemistry
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.