First synthesis of the A/B ring of ouabain.
[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.
Jung
Michael E
ME
Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA. jung@chem.ucla.edu
Piizzi
Grazia
G
D002316:Cardiotonic Agents / Q000138:chemical synthesis*; D004852:Epoxy Compounds / Q000737:chemistry; D007700:Kinetics; D010042:Ouabain / Q000138:chemical synthesis*; D013237:Stereoisomerism
D002316:Cardiotonic Agents; D004852:Epoxy Compounds; D010042:Ouabain