Stereocontrolled and Efficient Total Synthesis of (-)-Stephanotic Acid Methyl Ester and (-)-Celogentin C

被引：44

作者：

Hu, Weimin

Zhang, Fengying

Xu, Zhengren

Liu, Qiang

Cui, Yuxin

Jia, Yanxing ^{[1
]}

机构：

[1] Peking Univ, Sch Pharmaceut Sci, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 05期

基金：

中国国家自然科学基金;

关键词：

ANTIMITOTIC BICYCLIC PEPTIDES; CENTRAL TRYPTOPHAN RESIDUE; SUZUKI-MIYAURA REACTION; CELOGENTIN-C; CELOSIA-ARGENTEA; ASYMMETRIC-SYNTHESIS; STEPHANOTIC ACID; AMINO-ACIDS; LAPORTEA-MOROIDES; ORGANIC-SYNTHESIS;

D O I：

10.1021/ol902944f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A highly stereocontrolled and efficient total synthesis of (-)-stephanotic acid methyl ester and (-)-celogentin C was accomplished in longest linear 14 steps (4.6% overall yield) and in 20 steps (1.6% overall yield) from L-tryptophan, respectively. Highlights of the synthesis include a tandem asymmetric Michael addition/bromination/azidation strategy for a ready access to the leucine-tryptophan moiety (Leu-Trp linkage) and an oxidative coupling reaction to form the indole-imidazole linkage.

引用

页码：956 / 959

页数：4

共 45 条

[1] Total synthesis of stephanotic acid methyl ester [J].