Convergent Formal Synthesis of Ecteinascidin 743

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 pheno...

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Bibliographic Details
Published in:Journal of organic chemistry 2019-11, Vol.84 (21), p.13696-13706
Main Authors: Jia, Junhao, Chen, Ruijiao, Jia, Yuanliang, Gu, He, Zhou, Qin, Chen, Xiaochuan
Format: Article
Language:English
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Summary: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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.9b01778