Asymmetric Synthesis and Absolute Configuration of (+)- and (–)-Perhexiline

Chih-Chung Tseng; Iain R. Greig; William T. A. Harrison; Matteo Zanda

doi:10.1055/s-0035-1560708

Asymmetric Synthesis and Absolute Configuration of (+)- and (–)-Perhexiline

Chih-Chung Tseng, Iain R. Greig, William T. A. Harrison, Matteo Zanda

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Abstract

Racemic perhexiline has been used (or is currently undergoing clinical trials) for the treatment of a variety of cardiovascular disorders. Increasing evidence suggests that the (–)-enantiomer should be used, as opposed to the racemic mixture. Here, we report the first asymmetric synthesis of both enantiomers of perhexiline in high enantiomeric excess and the assignment of their (–)-S/(+)-R absolute stereochemistry by X-ray crystallography.

Original language	English
Pages (from-to)	73-78
Number of pages	6
Journal	Synthesis
Volume	48
Issue number	01
Early online date	27 Oct 2015
DOIs	https://doi.org/10.1055/s-0035-1560708
Publication status	Published - Jan 2016

Keywords

perhexiline
asymmetric analysis
stereochemistry
medicinal chemistry
crystal structure

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Accepted Manuscript
© Georg Thieme Verlag Stuttgart · New York. This is the accepted author manuscript, the final published version available at: https://www.thieme-connect.de/DOI/DOI?10.1055/s-0035-1560708
Accepted author manuscript, 292 KBLicence: Unspecified

William Harrison
- School of Natural & Computing Sciences, Chemistry - Personal Chair
Person: Academic

Cite this

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title = "Asymmetric Synthesis and Absolute Configuration of (+)- and (–)-Perhexiline",

abstract = "Racemic perhexiline has been used (or is currently undergoing clinical trials) for the treatment of a variety of cardiovascular disorders. Increasing evidence suggests that the (–)-enantiomer should be used, as opposed to the racemic mixture. Here, we report the first asymmetric synthesis of both enantiomers of perhexiline in high enantiomeric excess and the assignment of their (–)-S/(+)-R absolute stereochemistry by X-ray crystallography.",

keywords = "perhexiline, asymmetric analysis, stereochemistry, medicinal chemistry, crystal structure",

author = "Chih-Chung Tseng and Greig, {Iain R.} and Harrison, {William T. A.} and Matteo Zanda",

note = "We gratefully thank Signal Pharma for financial support and fellowship (C.C.T), and the EPSRC National Mass Spectrometry Service Centre (Swansea, UK) for performing HRMS analyses. We thank Prof Michael Frenneaux (University of East Anglia, Norwich, UK) for useful and stimulating discussions.",

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AU - Tseng, Chih-Chung

AU - Greig, Iain R.

AU - Harrison, William T. A.

AU - Zanda, Matteo

N1 - We gratefully thank Signal Pharma for financial support and fellowship (C.C.T), and the EPSRC National Mass Spectrometry Service Centre (Swansea, UK) for performing HRMS analyses. We thank Prof Michael Frenneaux (University of East Anglia, Norwich, UK) for useful and stimulating discussions.

PY - 2016/1

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N2 - Racemic perhexiline has been used (or is currently undergoing clinical trials) for the treatment of a variety of cardiovascular disorders. Increasing evidence suggests that the (–)-enantiomer should be used, as opposed to the racemic mixture. Here, we report the first asymmetric synthesis of both enantiomers of perhexiline in high enantiomeric excess and the assignment of their (–)-S/(+)-R absolute stereochemistry by X-ray crystallography.

AB - Racemic perhexiline has been used (or is currently undergoing clinical trials) for the treatment of a variety of cardiovascular disorders. Increasing evidence suggests that the (–)-enantiomer should be used, as opposed to the racemic mixture. Here, we report the first asymmetric synthesis of both enantiomers of perhexiline in high enantiomeric excess and the assignment of their (–)-S/(+)-R absolute stereochemistry by X-ray crystallography.

KW - perhexiline

KW - asymmetric analysis

KW - stereochemistry

KW - medicinal chemistry

KW - crystal structure

U2 - 10.1055/s-0035-1560708

DO - 10.1055/s-0035-1560708

M3 - Article

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EP - 78

JO - Synthesis

JF - Synthesis

SN - 0039-7881

IS - 01

ER -

Asymmetric Synthesis and Absolute Configuration of (+)- and (–)-Perhexiline

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William Harrison

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