A Convergent Stereoselective Total Synthesis of Racemic Phthoxazolin A
作者:Nadine Hénaff、Andrew Whiting
DOI:10.1021/ol990967b
日期:1999.10.1
[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.