The first total synthesis of natural grenadamide.

Org Biomol Chem

Department of Chemistry, University of Adelaide, South Australia 5005, Australia.

Published: January 2006


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Article Abstract

A concise, high yielding route to the naturally occurring enantiomer of grenadamide utilizing a 3,6-disubstituted 1,2-dioxine starting material is presented. The route allows for ease in synthesizing grenadamide derivatives varying at cyclopropyl carbons 2 and 3, with access to both enantiomers. Evidence for phosphorus-assisted deprotonation of 1,2-dioxines is also discussed.

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http://dx.doi.org/10.1039/b513774hDOI Listing

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