Toward an enantioselective synthesis of (-)-zampanolide: preparation of the C9-C20 region.
Progress toward the synthesis of the microtubule-stabilizing agent, (-)-zampanolide, is reported. Construction of the 2,6-cis-tetrahydropyran ring was accomplished utilizing ether transfer methodology in conjunction with an intramolecular radical cyclization reaction. Efficient installation of the C16-C20 side chain relied on a one-pot cross-metathesis/olefination sequence, Sharpless epoxidation, and selective reduction of a vinyl epoxide.
Department of Chemistry and Biochemistry and the Walther Cancer Research Center, University of Notre Dame, 251 Nieuwland Science Hall, Notre Dame, Indiana 46556-5670, USA.
Matthew R
MR
Wilson
Richard E
RE
Taylor
D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D008968:Molecular Conformation; D013237:Stereoisomerism
D018942:Macrolides; C444900:zampanolide