A convergent stereoselective total synthesis of racemic phthoxazolin A

被引:49
作者
Hénaff, N [1 ]
Whiting, A [1 ]
机构
[1] UMIST, Dept Chem, Manchester M60 1QD, Lancs, England
关键词
D O I
10.1021/ol990967b
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
[GRAPHICS] The first total synthesis of phthoxazolin A is reported which involves a convergent series of palladium-catalyzed cross coupling reactions to stereoselectively construct the Z,Z,E-trienyl unit of phthoxazolin A. The most important steps of the synthesis involve using vinylboronate pinacol ester as a vinyl dianion equivalent, by employing a Heck coupling of a vinyl iodide with the vinylboronate, followed by a deboronation-iodination sequence with inversion of alkene stereochemistry and Stille coupling of the resulting vinyl iodide.
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页码:1137 / 1139
页数:3
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