Hydroboration of Steroidal-1,5-dien-3β-ols : A General Procedure for the Introduction of a Hydroxyl Group at 1α-Position of the 3-Oxygenated Steroids

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The procedure used for the preparation of 1α-hydroxycholesterol from cholesta-1,4-dien-3-one was applied to 17,17-ethylenedioxyandrosta-1,4-dien-3-one and 20,20-ethylenedioxypregna-1,4-dien-3-one. The successful results described in this paper serve to provide a basis for evaluation of wide scope of this procedure for the introduction of a hydroxyl group at 1α-position of 3-oxygenated steroid derivatives. The procedure consists of three steps starting from 3-keto-△^<1,4>-steroids available readily from 3-oxygenated steroids : 1) deconjugation to 3-keto-△^<1,5>-steroids, 2) reduction with metalhydride to 3β-hydroxy-△^<1,5>-steroids, and 3) hydroboration to 1α, 3β-dihydroxy-△^5-steroids. This paper also includes definite identification of the final and intermediate compounds in the procedure and interpretation of their mass and nuclear magnetic resonance spectroscopic behaviors.
社団法人日本薬学会の論文
1974-09-25