Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors

被引：146

作者：

DeLorbe, John E. ^{[1
]}

Jabri, Salman Y. ^{[1
]}

Mennen, Steven M. ^{[1
]}

Overman, Larry E. ^{[1
]}

Zhang, Fang-Li ^{[1
]}

机构：

[1] Univ Calif Irvine, Dept Chem, Irvine, CA 92697 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2011年 / 133卷 / 17期

关键词：

GLIOTOXIN; AGENT; INHIBITOR; INDUCTION; CHAETOCIN; OXIDATION; ANALOGS;

D O I：

10.1021/ja201789v

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

A concise second-generation total synthesis of the fungal-derived alkaloid (+)-gliocladin C (11) in 10 steps and 1196 overall yield from isatin is reported. In addition, the epipolythiodioxopiperazine (ETP) natural product (+)-gliocladine C (6) has been prepared in six steps and 2996 yield from the di-(tert-butoxycarbonyl) precursor of 11. The total synthesis of 6 constitutes the first total synthesis of an ETP natural product containing a hydroxyl substituent adjacent to a quaternary carbon stereocenter in the pyrrolidine ring.

引用

收藏

页码：6549 / 6552

页数：4

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