Key Laboratory of Green Chemistry and Technology of Ministry of Education, College of Chemistry , Sichuan University , Chengdu 610064 , P.R. China.
Jining Medical College , Jining 272067 , P.R. China.
J Org Chem. 2019 Nov 1;84(21):13696-13706. doi: 10.1021/acs.joc.9b01778. Epub 2019 Oct 1.
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.
本文描述了埃替拉辛 743 的简洁式综合。关键特征包括多取代的四氢异喹啉和苯丙氨醇部分通过区域和立体选择性的Pictet-Spengler 环化反应偶联，以及随后对酚羟基的化学选择性 MOM 保护，这为理想的五环化合物提供了快速通道。该合成成功地通过芝麻酚的特征大环内酯从 23 步反应中获得了所需的高级中间体。
