A novel palladium-mediated coupling approach to 2,3-disubstituted benzo[b]thiophenes and its application to the synthesis of tubulin binding agents

被引：237

作者：

Flynn, BL ^{[1
]}

Verdier-Pinard, P

Hamel, E

机构：

[1] Australian Natl Univ, The Fac, Dept Chem, Canberra, ACT 0200, Australia

[2] NCI, Frederick Canc Res & Dev Ctr, Div Canc Treatment & Diag, Dev Therapeut Program,Screening Technol Branch, Frederick, MD 21702 USA

来源：

ORGANIC LETTERS | 2001年 / 3卷 / 05期

关键词：

D O I：

10.1021/ol0067179

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] Flexible, convergent access to 2,3-disubstituted benzo[b]thiophenes has been developed. The most concise approach involves sequential coupling of o-bromoiodobenzenes with benzylmercaptan and zinc acetylides to give benzyl o-ethynylphenyl sulfides which react with iodine to give 3-iodobenzo[b]thiophenes in a 5-endo-dig iodocyclization. These iodides can be further elaborated using palladium-mediated coupling and/or metalation techniques. This method has been applied to the synthesis of some novel tubulin binding agents.

引用

页码：651 / 654

页数：4

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