Study of Cascade Ring-Closing Metathesis Reactions en Route to an Advanced Intermediate of Taxol.

J Org Chem

WestCHEM, School of Chemistry, University of Glasgow, Joseph Black Building , University Avenue, Glasgow G12 8QQ, U.K.

Published: December 2016

A highly functionalized intermediate in the synthesis of Taxol has been synthesized, which features the tricyclic core and the required oxygen substituents at C1, C2, C7, C10, and C13. The key step, a ring-closing dienyne metathesis (RCDEYM) reaction, has been thoroughly optimized to favor the tricyclic product over the undesired bicyclic product resulting from diene metathesis.

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http://dx.doi.org/10.1021/acs.joc.6b02264DOI Listing

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