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Synthesis of isomeric 16,17‐epoxy‐[17‐ 3 H)‐derivatives of 3‐hydroxy and 3‐methoxy‐oestra‐1,3,5(10)‐trienes
Author(s) -
Blackburn G. Michael,
Taylor Brian F.,
Worrall Andrew F.
Publication year - 1986
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.2580230210
Subject(s) - chemistry , deuterium , epoxy , nuclear magnetic resonance spectroscopy , isotope , kinetic isotope effect , chemical synthesis , medicinal chemistry , stereochemistry , organic chemistry , nuclear physics , physics , biochemistry , in vitro
Deuterium NMR spectroscopy has been used to show that a previously published synthesis of 16α, 17α‐epoxy ‐3‐hydroxy‐[17‐ 3 H]oestra‐1,3,5(10)‐triene is not regiospecific but leads to additional isotope incorporation at positions ‐2 and/or ‐4. A modified synthesis is described which leads to the title compounds exclusively labelled at position ‐17.