Synthesis and Stereochemical Assignment of (+)-Chamuvarinin

Synthesis and Stereochemical Assignment of (+)-Chamuvarinin

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 constitute...

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Veröffentlicht in:Organic letters 2011-02, Vol.13 (3), p.514-517
Hauptverfasser: Florence, Gordon J., Morris, Joanne C., Murray, Ross G., Osler, Jonathan D., Reddy, Vanga R., Smith, Terry K.
Format: Artikel
Sprache:eng
Schlagworte:
Acetogenins - chemical synthesis
Acetogenins - chemistry
Letter
Molecular Structure
Plant Roots - chemistry
Stereoisomerism
Uvaria - chemistry
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Zusammenfassung: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.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol1028699