Ruthenium-Catalyzed Oppenauer-Type Oxidation of 3β-Hydroxy Steroids. A Highly Efficient Entry into the Steroidal Hormones with 4-En-3-one Functionality

…, P Kočovský, JE Bäckvall

Index: Almeida, Maria L. S.; Kocovsky, Pavel; Backvall, Jan-E. Journal of Organic Chemistry, 1996 , vol. 61, # 19 p. 6587 - 6590

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Citation Number: 67

Abstract

Oxidation of 5-unsaturated 3β-hydroxy steroids 1 to the corresponding 4-en-3-one derivatives 2 can be performed efficiently by acetone at reflux in the presence of a catalytic system consisting of either (PPh3) 3RuCl2 (3) and K2CO3 or [(C4Ph4COHOCC4Ph4)(μ- H)][(CO) 4Ru2](4). The reaction proceeds via a ruthenium-catalyzed dehydrogenation of 1 and subsequent hydrogen transfer to acetone with concomitant double bond migration.

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