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Synthesis and stereochemical assignment of (+)-chamuvarinin

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Author(s)

Gordon John Florence, Joanne Charleen Morris, Ross George Murray, Jonathan Osler, Raghava Reddy Vanga, Terry K Smith

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Abstract

A stereocontrolled total synthesis of (+)-chamuvarinin, isolated from the root extract of Uvaria Chamae, utilizes a convergent modular strategy to construct the adjacently linked C15−C28 ether array, followed by a late-stage Julia−Kocienski olefination to append the butenolide motif. This constitutes the first total synthesis of (+)-chamuvarinin, defining the relative and absolute configuration of this unique annonaceous acetogenin.
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Original languageEnglish
Pages (from-to)514-517
Number of pages4
JournalOrganic Letters
Volume13
Issue number3
Early online date21 Dec 2010
DOIs
Publication statusPublished - 4 Feb 2011

    Research areas

  • Hydrolytic kinetic resolution, Annonaceous acetogenins, Uvaria-chamae, Stereoisomer library, Recent progress, Mosher method, Bearing, Condensation, Mechanisms, Murisolins

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