Stereospecific Synthesis of Steroidal 20,16-γ-Carbolactones
- 1 November 1998
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 28 (21) , 4043-4057
- https://doi.org/10.1080/00397919808004965
Abstract
Two strategies have been explored for the synthesis of steroidal 20,16-γ-carbolactones from the corresponding 17-ketoandrostane. A highly efficient, stereospecific protocol has been developed for the β-oriented cis-γ-lactone, based on a Michael addition of cyanide to a conjugated ketone. A different approach, involving prior attachment of a 3-carbon side chain on C-17 of a 17-oxo-16β-acetoxy-androstane led to the epimeric, α-oriented lactone.Keywords
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