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

被引:30
作者
Lemiere, Gilles [1 ]
Sedehizadeh, Simon [1 ]
Toueg, Julie [1 ]
Fleary-Roberts, Nadia [1 ]
Clayden, Jonathan [1 ]
机构
[1] Univ Manchester, Sch Chem, Manchester M13 9PL, Lancs, England
基金
英国工程与自然科学研究理事会;
关键词
VIVO SEIZURE INDUCTION; CHIRAL LITHIUM AMIDES; DOMOIC ACID; DEAROMATISING CYCLIZATION; ISODOMOIC ACIDS; STEREOSELECTIVE-SYNTHESIS; ASYMMETRIC-SYNTHESIS; RED ALGA; ISOMERS; IDENTIFICATION;
D O I
10.1039/c1cc00048a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:3745 / 3747
页数:3
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