Concise Total Synthesis of (+)-Luteoalbusins A and B

被引：35

作者：

Adams, Timothy C. ^{[1
]}

Payette, Joshua N. ^{[1
]}

Cheah, Jaime H. ^{[2
]}

Movassaghi, Mohammad ^{[1
]}

机构：

[1] MIT, Dept Chem, Cambridge, MA 02139 USA

[2] MIT, Koch Inst Integrat Canc Res, Cambridge, MA 02139 USA

来源：

ORGANIC LETTERS | 2015年 / 17卷 / 17期

基金：

美国国家科学基金会;

关键词：

ENANTIOSELECTIVE TOTAL-SYNTHESIS; EPIPOLYTHIODIKETOPIPERAZINE ALKALOIDS; GENERAL-APPROACH; IN-VIVO; PREPARING EPIDITHIODIOXOPIPERAZINES; TRIOXOPIPERAZINE PRECURSORS; ANTIBIOTICS GLIOTOXIN; ARYL PYRROLOINDOLINES; MESO-CHIMONANTHINE; CELL PROLIFERATION;

D O I：

10.1021/acs.orglett.5b02059

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The first total synthesis of (+)-luteoalbusins A and B is described. Highly regio- and diastereoselective chemical transformations in our syntheses include a Friedel-Crafts C3-indole addition to a cydotryptophan-derived diketopiperazine, a late-stage diketopiperazine dihydroxylation, and a C11-sulfidation sequence, in addition to congener-specific polysulfane synthesis and cyclization to the corresponding epipolythiodiketopiperazine. We also report the cytoxicity of both alkaloids, and closely related derivatives, against A549, He La, HCT116, and MCF7 human cancer cell lines.

引用

收藏

页码：4268 / 4271

页数：4

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