A convergent stereoselective total synthesis of racemic phthoxazolin A
A convergent stereoselective total synthesis of racemic phthoxazolin A
复制标题
DOI：
10.1021/ol990967b
复制
发表时间：
1999-10-07
期刊：
影响因子：
5.2
通讯作者：
Whiting, A
中科院分区：
文献类型：
--
作者：
Hénaff, N;Whiting, A
[图解]首次报道了邻苯二甲唑啉A的全合成，它涉及一系列钯催化的交叉偶联反应，以立体选择性地构建邻恶唑啉A的Z，Z，E-三烯基单元。合成的最重要的步骤包括使用乙烯基硼酸酯作为乙烯基二阴离子的等价物，通过使用乙烯基碘与乙烯基硼酸酯的Heck偶联，然后通过烯烃立体化学的反转和得到的乙烯基碘的Stille偶联来进行去配位-碘化反应。
[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.