Issue 13, 2011
From the journal:

Chemical Communications

A general synthetic approach to the amnesic shellfish toxins: total synthesis of (−)-isodomoic acid B, (−)-isodomoic acid E and (−)-isodomoic acid F†

Gilles Lemière,a   Simon Sedehizadeh,a   Julie Toueg,a   Nadia Fleary-Robertsa  and  Jonathan Clayden*a  

* Corresponding authors

a School of Chemistry, University of Manchester, Oxford Rd., Manchester M13 9PL, UK
E-mail: clayden@man.ac.uk
Fax: +44 161 275 4612

Abstract

The alkynylpyrrolidine 4 was made via a dearomatising cyclisation of an aromatic amide, and was elaborated by stannylcupration and palladium-catalysed coupling to achieve the first total synthesis of three members of the isodomoic acid family; the same alkyne can be envisaged as a precursor to several more of this class of amnesic shellfish toxins.

Graphical abstract: A general synthetic approach to the amnesic shellfish toxins: total synthesis of (−)-isodomoic acid B, (−)-isodomoic acid E and (−)-isodomoic acid F

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Article information

DOI
https://doi.org/10.1039/C1CC00048A
Article type
Communication
Submitted
04 Jan 2011
Accepted
31 Jan 2011
First published
24 Feb 2011

Chem. Commun., 2011,47, 3745-3747

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A general synthetic approach to the amnesic shellfish toxins: total synthesis of (−)-isodomoic acid B, (−)-isodomoic acid E and (−)-isodomoic acid F

G. Lemière, S. Sedehizadeh, J. Toueg, N. Fleary-Roberts and J. Clayden, Chem. Commun., 2011, 47, 3745 DOI: 10.1039/C1CC00048A

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