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

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.