Steroids p. 249 - 260 (1986)
Update date:2022-08-03
Topics:
Wiebe, J. P.
Dave, Vinod
Stothers, J. B.
Recently several allylic steroids have been found in gonadal and breast tissues.In order to establish their presence and identity in tissues and determine the possible biological properties, a method for the synthesis of 4-pregnene-3α,20α-diol, 4-pregnene-3α,20β-diol, 4-pregnene-3β,20α-diol, and 4-pregnene-3β,20β-diol was developed using 4-pregnene-3,20-dione (progesterone) as substrate and freshly-prepared aluminum isopropoxide in isopropyl alcohol as reducing agent.The yields were about 19percent, 30percent, 13percent, and 38percent for the 3α,20α-, 3α,20β-, 3β,20α-, and 3β,20β-diols, respectively.The structures and stereochemistry of these diols were established using proton and carbon NMR spectroscopy and infrared and mass spectrometry.
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