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A Concise and Practical Semisynthesis of Ecteinascidin 743 and (–)‐Jorumycin
Author(s) -
Xu Shanghu,
Wang Guan,
Zhu Jinjin,
Shen Chuang,
Yang Zhezhou,
Yu Jun,
Li Zhong,
Lin Tanghuan,
Sun Xun,
Zhang Fuli
Publication year - 2017
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201601409
Subject(s) - semisynthesis , chemistry , tetrahydroisoquinoline , yield (engineering) , stereochemistry , combinatorial chemistry , metallurgy , materials science
Ecteinascidin 743 is an antitumor drug used to treat specific soft‐tissue sarcomas (STS). In this paper, we present a concise and practical semisynthesis of ecteinascidin 743 starting from safracin B. The strategy involves the direct conversion of an aliphatic amino group into an acetoxy group. By this approach, ecteinascidin 743 was synthesized in 14 steps and 1.5 % overall yield. The synthetic approach also provided access to other tetrahydroisoquinoline alkaloids, such as (–)‐jorumycin (a promising anticancer candidate). (–)‐Jorumycin was prepared in six steps and 24.1 % overall yield from safracin B.