Synthesis and stereochemical assignment of (+)-chamuvarinin

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

doi:10.1021/ol1028699

Synthesis and stereochemical assignment of (+)-chamuvarinin

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

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)	514-517
Number of pages	4
Journal	Organic Letters
Volume	13
Issue number	3
Early online date	21 Dec 2010
DOIs	https://doi.org/10.1021/ol1028699
Publication status	Published - 4 Feb 2011

Keywords

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

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10.1021/ol1028699

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(c)2011 American Chemical Society. This article is open access under the ACS AuthorChoice option.
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3 Finished

RS Uni Research Fellowship Renewal 2010: University Research Fellowship - New Methods and Strategies for the Synthesis of Bioactive Natural Products
Florence, G. J. (PI)
1/10/10 → 30/09/13
Project: Fellowship
Validating choline metabolism WT: validating choline metabolism as a drug target in the fight against T Brucei
Smith, T. K. (PI)
The Wellcome Trust
1/12/09 → 30/11/11
Project: Standard
Synthesis of Palmerolides EP/F011458/1: Synthesis of the Palmerolides
Florence, G. J. (PI)
EPSRC
1/11/07 → 30/04/11
Project: Standard

2 Article

Non-natural acetogenin analogues as potent Trypanosoma brucei inhibitors
Florence, G. J., Fraser, A. L., Gould, E. R., King, E. F. B., Menzies, S. K., Morris, J. C., Tulloch, L. B. & Smith, T. K., Nov 2014, In: ChemMedChem. 9, 11, p. 2548-2556 9 p.
Research output: Contribution to journal › Article › peer-review

Open Access
File
Total synthesis, stereochemical assignment and biological activity of chamuvarinin and structural analogues
Florence, G. J., Morris, J. C., Murray, R. G., Vanga, R. R., Osler, J. & Smith, T. K., 17 Jun 2013, In: Chemistry - A European Journal. 19, 25, p. 8309-8320 12 p.
Research output: Contribution to journal › Article › peer-review

Cite this

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title = "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.",

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

author = "Florence, {Gordon John} and Morris, {Joanne Charleen} and Murray, {Ross George} and Jonathan Osler and Vanga, {Raghava Reddy} and Smith, {Terry K}",

note = "Supported by grants from EPSRC (EP/F011458/1) and The Wellcome Trust (086658).",

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doi = "10.1021/ol1028699",

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T1 - Synthesis and stereochemical assignment of (+)-chamuvarinin

AU - Florence, Gordon John

AU - Morris, Joanne Charleen

AU - Murray, Ross George

AU - Osler, Jonathan

AU - Vanga, Raghava Reddy

AU - Smith, Terry K

N1 - Supported by grants from EPSRC (EP/F011458/1) and The Wellcome Trust (086658).

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 - Hydrolytic kinetic resolution

KW - Annonaceous acetogenins

KW - Uvaria-chamae

KW - Stereoisomer library

KW - Recent progress

KW - Mosher method

KW - Bearing

KW - Condensation

KW - Mechanisms

KW - Murisolins

U2 - 10.1021/ol1028699

DO - 10.1021/ol1028699

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SN - 1523-7060

VL - 13

SP - 514

EP - 517

JO - Organic Letters

JF - Organic Letters

IS - 3

ER -

Synthesis and stereochemical assignment of (+)-chamuvarinin

Abstract

Keywords

Access to Document

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Projects

RS Uni Research Fellowship Renewal 2010: University Research Fellowship - New Methods and Strategies for the Synthesis of Bioactive Natural Products

Validating choline metabolism WT: validating choline metabolism as a drug target in the fight against T Brucei

Synthesis of Palmerolides EP/F011458/1: Synthesis of the Palmerolides

Research output

Non-natural acetogenin analogues as potent Trypanosoma brucei inhibitors

Total synthesis, stereochemical assignment and biological activity of chamuvarinin and structural analogues

Cite this