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First synthesis of the A/B ring of ouabain
Michael E Jung1, Grazia Piizzi
1Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA. jung@chem.ucla.edu
Organic Letters
|January 17, 2003
Abstract:
[reaction: see text] The synthesis of the fully fuctionalized A/B ring of ouabain has been accomplished efficiently from commercially available starting materials. A key Robinson annulation allows for the building of the desired carbon framework in one high-yielding step. Directed epoxidation followed by selective epoxide opening furnished the final tetraol with the desired all-cis stereochemistry.