Affordable Access

Publisher Website

Enol dependent reactions of β,γ-unsaturated ketones, 10β-fluoro-17α-ethynyl-19-nortestosterone, a potent estrogen

Authors
Journal
Steroids
0039-128X
Publisher
Elsevier
Publication Date
Volume
1
Issue
1
Identifiers
DOI: 10.1016/s0039-128x(63)80152-x

Abstract

The reaction of several estr-5(10)-en-3-ones with perchloryl fluoride and with N-chlorosuccinimide led to the 10β-fluoro- and 10β-chloro-19-nortestosterone derivatives. These reactions probably proceed via the Δ3,5(10)-enol rather than through the conjugate anion. 10β-Fluoro-17α-ethynyl-19-nortestosterone (IIa) was completely stable to attempted base-catalyzed dehydrofluorination while the corresponding 10β-chloro derivative (IIb) was readily converted to the estra-4,9(10)-diene compound (III). IIa exhibited striking estrogenic potency which is believed to be a property of the compound per se.

There are no comments yet on this publication. Be the first to share your thoughts.