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Issue 2, 2006
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The first total synthesis of natural grenadamide

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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.

Graphical abstract: The first total synthesis of natural grenadamide

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Publication details

The article was received on 28 Sep 2005, accepted on 04 Nov 2005 and first published on 12 Dec 2005


Article type: Paper
DOI: 10.1039/B513774H
Citation: Org. Biomol. Chem., 2006,4, 323-330
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    The first total synthesis of natural grenadamide

    T. D. Avery, J. A. Culbert and D. K. Taylor, Org. Biomol. Chem., 2006, 4, 323
    DOI: 10.1039/B513774H

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