Convergent Formal Synthesis of Ecteinascidin 743
Convergent Formal Synthesis of Ecteinascidin 743
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Ecteinascidin 743 的收敛形式合成
DOI：
10.1021/acs.joc.9b01778
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发表时间：
2019
影响因子：
3.6
通讯作者：
Chen Xiaochuan
中科院分区：
文献类型：
--
作者：
Jia Junhao;Chen Ruijiao;Jia Yuanliang;Gu He;Zhou Qin;Chen Xiaochuan
描述了海鞘素743的一种简洁的形式化合成。关键特征涉及通过区域和立体选择性Pictet-Spengler环化以及随后的苯酚基团的化学选择性双保护的多取代的四氢异喹啉和苯丙氨醇部分的偶联，这打开了快速获得所需的pentaclitazone的途径。该方法经23步反应成功地从芝麻素中得到了具有特征性的大环内酯高级中间体。
A concise formal synthesis of ecteinascidin 743 is described. Key features involve the coupling of the multisubstituted tetrahydroisoquinoline and phenylalaninol moieties via a regio- and stereoselective Pictet–Spengler cyclization as well as the subsequent chemoselective MOM protection of the phenol group, which opens a rapid access to the desirable pentacycle. The synthesis successfully delivered the advanced intermediate with the characteristic macrolactone from sesamol in 23 steps.