Issue 2, 2006
From the journal:

Organic & Biomolecular Chemistry

The first total synthesis of natural grenadamide†

Thomas D. Avery,a   Julie A. Culberta  and  Dennis K. Taylor*a  

* Corresponding authors

a Department of Chemistry, University of Adelaide, dennis.taylor@adelaide.edu.au , South Australia, Australia

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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Article information

DOI
https://doi.org/10.1039/B513774H
Article type
Paper
Submitted
28 Sep 2005
Accepted
04 Nov 2005
First published
12 Dec 2005

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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