Enantioselective and Collective Total Syntheses of Xanthanolides
Enantioselective and Collective Total Syntheses of Xanthanolides
复制标题
黄嘌呤内酯的对映选择性和集体全合成
DOI：
10.1002/anie.201710846
复制
发表时间：
2017-12-18
影响因子：
16.6
通讯作者：
Tang, Yefeng
中科院分区：
文献类型：
--
作者：
Feng, Juan;Lei, Xiaoqiang;Tang, Yefeng
报道了手性磷酸催化的串联烯丙基硼化/内酯化反应对映体选择性合成(+)-8-表黄原素。以(+)-8-表-黄原素为前驱体，合成了一系列具有挑战性的黄乙醇内酯。其中，黄原虫内酯是最复杂的黄乙醇内酯单体之一，它是通过生物激发的串联双键异构化/6pi电子环化/分子内Diels-Alder反应获得的，而品红内酯A、B、D、E和L-N是一组黄乙醇内酯二聚体，通过生物激发Diels-Alder二聚体和后期多样化得到。
An enantioselective synthesis of (+)-8-epi-xanthatin hinging on a chiral phosphoric acid catalyzed tandem allylboration/lactonization reaction is reported. With (+)-8-epi-xanthatin as the precursor, the collective synthesis of a series of synthetically challenging xanthanolides was also accomplished. Among them, xanthipungolide, one of the most complex xanthanolide monomers, was accessed through a bioinspired tandem double-bond isomerization/6 pi electronic cyclization/intramolecular Diels-Alder reaction, and pungiolides A, B, D, E, and L-N, a group of xanthanolide dimers, were assembled through a bioinspired Diels-Alder dimerization followed by late-stage diversification.