Synthesis of the putative structures of homopumiliotoxins 235C and 233F

P. Armstrong; S. Feutren; H. McAlonan; G. O'Mahony; Paul Stevenson

doi:10.1016/j.tetlet.2003.12.126

Synthesis of the putative structures of homopumiliotoxins 235C and 233F

P. Armstrong, S. Feutren, H. McAlonan, G. O'Mahony, Paul Stevenson

School of Chemistry and Chemical Engineering

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

12 Citations (Scopus)

Abstract

A novel approach to diene based quinolizidines, using an intramolecular Heck reaction in which the vinyl bromide double bond undergoes inversion of configuration, is reported. These quinolizidines have previously been proposed as tentative structures for homopumiliotoxin alkaloids 233F and 235C. The mass spectral data of the synthetic materials were different to those of the natural products confirming that the original structures need to be revised. (C) 2004 Elsevier Ltd. All rights reserved.

Original language	English
Pages (from-to)	1627-1630
Number of pages	4
Journal	Tetrahedron Letters
Volume	45
Issue number	8
DOIs	https://doi.org/10.1016/j.tetlet.2003.12.126
Publication status	Published - 16 Feb 2004

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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title = "Synthesis of the putative structures of homopumiliotoxins 235C and 233F",

abstract = "A novel approach to diene based quinolizidines, using an intramolecular Heck reaction in which the vinyl bromide double bond undergoes inversion of configuration, is reported. These quinolizidines have previously been proposed as tentative structures for homopumiliotoxin alkaloids 233F and 235C. The mass spectral data of the synthetic materials were different to those of the natural products confirming that the original structures need to be revised. (C) 2004 Elsevier Ltd. All rights reserved.",

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AU - Armstrong, P.

AU - Feutren, S.

AU - McAlonan, H.

AU - O'Mahony, G.

AU - Stevenson, Paul

PY - 2004/2/16

Y1 - 2004/2/16

N2 - A novel approach to diene based quinolizidines, using an intramolecular Heck reaction in which the vinyl bromide double bond undergoes inversion of configuration, is reported. These quinolizidines have previously been proposed as tentative structures for homopumiliotoxin alkaloids 233F and 235C. The mass spectral data of the synthetic materials were different to those of the natural products confirming that the original structures need to be revised. (C) 2004 Elsevier Ltd. All rights reserved.

AB - A novel approach to diene based quinolizidines, using an intramolecular Heck reaction in which the vinyl bromide double bond undergoes inversion of configuration, is reported. These quinolizidines have previously been proposed as tentative structures for homopumiliotoxin alkaloids 233F and 235C. The mass spectral data of the synthetic materials were different to those of the natural products confirming that the original structures need to be revised. (C) 2004 Elsevier Ltd. All rights reserved.

U2 - 10.1016/j.tetlet.2003.12.126

DO - 10.1016/j.tetlet.2003.12.126

M3 - Article

VL - 45

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EP - 1630

JO - Tetrahedron Letters

JF - Tetrahedron Letters

SN - 0040-4039

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