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Synthetic approach to analogues of 19-norsteroids with an acyclic side chain

Authors
Journal
Steroids
0039-128X
Publisher
Elsevier
Publication Date
Volume
53
Identifiers
DOI: 10.1016/0039-128x(89)90149-9
Disciplines
  • Biology
  • Chemistry

Abstract

Abstract Racemic 14β-hydroxy-3-methoxy-8α,9α-1,3 5(10)-estratriene-17-one (I), obtained by total synthesis, was converted into a derivative with alkoxycarbonyl-ethylenic side chain, rac-(20E)-21-methoxycarbonyl-19-nor-8α,9α-pregna-1,3,5(10), 20-tetraene-3, 14β-diol 3-methyl ether (XII) using two Wittig reactions. Analogous derivatives of 5α-androstane were prepared as synthetic models. In the estrane series the stereochemistry of attachement of the side chain in position 17, biological activity of some compounds, and their chromatographic properties were investigated.

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