Synthesis and Stereochemical Assignment of (+)-Chamuvarinin

Raghava Vanga; G. J. Florence; J. Morris; R. Murray; J. Osler; T. Smith

doi:10.1021/ol1028699

Synthesis and Stereochemical Assignment of (+)-Chamuvarinin

Raghava Vanga, G. J. Florence, J. Morris, R. Murray, J. Osler, T. Smith

Faculty of Life Sciences and Education

Research output: Contribution to journal › Article › peer-review

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.

Original language	English
Pages (from-to)	5 - 7
Number of pages	2
Journal	Organic Letters
Volume	13
Issue number	3
DOIs	https://doi.org/10.1021/ol1028699
Publication status	Published - 4 Feb 2011

Keywords

chamuvarinin
synthesis and stereochemical

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10.1021/ol1028699Licence: CC BY-NC-ND

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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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AU - Vanga, Raghava

AU - Florence, G. J.

AU - Morris, J.

AU - Murray, R.

AU - Osler, J.

AU - Smith, T.

PY - 2011/2/4

Y1 - 2011/2/4

N2 - 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.

AB - 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.

KW - chamuvarinin

KW - synthesis and stereochemical

U2 - 10.1021/ol1028699

DO - 10.1021/ol1028699

M3 - Article

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JO - Organic Letters

JF - Organic Letters

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ER -

Synthesis and Stereochemical Assignment of (+)-Chamuvarinin

Abstract

Keywords

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