SYNTHESIS AND CHARACTERISTICS OF ALLYLIC 4-PREGNENE-3,20-DIOLS FOUND IN GONADAL AND BREAST TISSUES

Article abstract of DOI:10.1016/0039-128X(86)90095-4

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.