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Synthesis and stereochemical assignment of (+)-chamuvarinin.


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.

SUBMITTER: Florence GJ 

PROVIDER: S-EPMC3031177 | biostudies-literature | 2011 Feb

REPOSITORIES: biostudies-literature

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Synthesis and stereochemical assignment of (+)-chamuvarinin.

Florence Gordon J GJ   Morris Joanne C JC   Murray Ross G RG   Osler Jonathan D JD   Reddy Vanga R VR   Smith Terry K TK  

Organic letters 20101221 3


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. ...[more]

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