Asymmetric synthesis of highly functionalized tyrosine derivatives for the construction of bistetrahydroisoquinoline alkaloids

被引：3

作者：

Du, Enming

Pan, Xuan

Guan, Baohe

Liu, Zhanzhu ^{[1
]}

机构：

[1] Peking Union Med Coll, State Key Lab Bioact Subst & Funct Nat Med, Inst Mat Med, Beijing 100050, Peoples R China

来源：

TETRAHEDRON LETTERS | 2018年 / 59卷 / 31期

关键词：

Bistetrahydroisoquinoline alkaloid; Tyrosine derivatives; Asymmetric synthesis; L-tyrosine; (-)-CRIBROSTATIN-4 RENIERAMYCIN-H; BENZYNE-FURAN CYCLOADDITIONS; B-2; METHYL-ESTER; (-)-RENIERAMYCIN G; ECTEINASCIDIN-743; (-)-SAFRAMYCIN; (-)-JORUMYCIN; CYTOTOXICITY; CONDENSATION; SAFRAMYCINS;

D O I：

10.1016/j.tetlet.2018.07.003

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel and facile synthesis of L-5-hydroxy-2,4-methoxy-3-methylphenylalanine derivatives, which are the key coupling partners for the asymmetric total synthesis of natural bistetrahydroisoquinoline alkaloids, is realized starting from L-tyrosine with 17% overall yield. The synthesis has been carried out on a multigram scale featuring the following key steps: (a) transformation of phenol to dihydroquinone via salcomine-catalyzed oxidation followed by zinc-acetic acid reduction; (b) single TBS-protection of dihydroquinone; (c) Mitsunobu methylation of the newly generated phenolic hydroxyl group. (C) 2018 Elsevier Ltd. All rights reserved.

引用

页码：3029 / 3032

页数：4

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