Total synthesis of dysiherbaine.

J Org Chem

Department of Chemistry, University of California, Irvine 92697-2025, USA.

Published: May 2002

A convergent total synthesis of the marine natural product dysiherbaine was accomplished. The key steps of the synthesis are an alkylation at the gamma-carbon of a protected glutamate with a highly substituted pyran derived from mannose, which was followed by a ring-contraction cascade reaction, which simultaneously gave the tetrasubstituted carbon and the hexahydrofuro[3,2-b]pyran ring system of the natural product.

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http://dx.doi.org/10.1021/jo0107610DOI Listing

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