Synthesis of the allylic gonadal steroids, 3 α-hydroxy-4-pregnen-20-one and 3 α-hydroxy-4-androsten-17-one, and of 3 α-hydroxy-5 α-pregnan-20-one

A method for the convenient synthesis of the recently isolated allylic gonadal steroids, 3 α-hydroxy-4-pregnen-20-one (3 α-dihydroprogesterone; 3 α-DHP) and 3 α-hydroxy-4-androsten-17-one (3 α-HA), was developed using 4-pregnene-3,20-dione (progesterone) and 4-androstene-3,17-dione as substrates and...

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Published inSteroids Vol. 45; no. 1; pp. 39 - 51
Main Authors Wiebe, J.P., Deline, C., Buckingham, K.D., Dave, Vinod, Stothers, J.B.
Format Journal Article
LanguageEnglish
Published NEW YORK Elsevier Inc 1985
Elsevier
Elsevier Science
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Summary:A method for the convenient synthesis of the recently isolated allylic gonadal steroids, 3 α-hydroxy-4-pregnen-20-one (3 α-dihydroprogesterone; 3 α-DHP) and 3 α-hydroxy-4-androsten-17-one (3 α-HA), was developed using 4-pregnene-3,20-dione (progesterone) and 4-androstene-3,17-dione as substrates and potassium trisiamylborohydride (KS-Selectride) as reducing agent. Similar reactions were also used for the reduction of 5 α-pregnane-3,20-dione to 3 α-hydroxy-5 α-pregnan-20-one (3 α-HP). The yields were about 15%, 50%, and >90% for 3 α-DHP, 3 α-HA and 3 α-HP, respectively. Structures of the products, including the 3 β-isomers and the 17 α-epimer, formed in these reactions were determined by NMR and mass spectroscopic methods.
Bibliography:ObjectType-Article-1
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ISSN:0039-128X
1878-5867
DOI:10.1016/0039-128X(85)90064-9