Highly stereoselective palladium catalysed cross-coupling approaches to the total synthesis of phthoxazolin A

被引：52

作者：

Hénaff, N ^{[1
]}

Whiting, A ^{[1
]}

机构：

[1] UMIST, Dept Chem, Manchester M60 1QD, Lancs, England

来源：

TETRAHEDRON | 2000年 / 56卷 / 29期

关键词：

phthoxazolin A; Heck and Stille couplings;

D O I：

10.1016/S0040-4020(00)00182-4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of racemic Phthoxazolin A 4 is described, involving a convergent series of palladium cross-coupling reactions to stereoselectively construct the ZZ,E-trienyl unit. The most important steps involve using vinylboronate pinacol ester 1 as a vinyl dianion equivalent, by employing a Heck coupling of a vinyl iodide 9 with the vinyl boronate 1, followed by a deboronation-iodination sequence with inversion of alkene stereochemistry to provide a new alkenyl iodide 6. Final Stille coupling of the vinyl iodide 6 with an oxazolyl alkenyl stannane 40 provided Phthoxazolin A 4. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：5193 / 5204

页数：12

共 73 条

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