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

…, S Sedehizadeh, J Toueg, N Fleary-Roberts…

Index: Lemiere, Gilles; Sedehizadeh, Simon; Toueg, Julie; Fleary-Roberts, Nadia; Clayden, Jonathan Chemical Communications, 2011 , vol. 47, # 13 p. 3745 - 3747

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Citation Number: 16

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.