Enantiospecific Total Synthesis of the Hapalindoles, Fischerindoles, and Welwitindolinones via a Redox Economic Approach

被引：240

作者：

Richter, Jeremy M. ^{[1
]}

Ishihara, Yoshihiro ^{[1
]}

Masuda, Takeshi ^{[1
]}

Whitefield, Brandon W. ^{[1
]}

Llamas, Tomas ^{[1
]}

Pohjakallio, Antti ^{[1
]}

Baran, Phil S. ^{[1
]}

机构：

[1] Scripps Res Inst, Dept Chem, La Jolla, CA 92037 USA

来源：

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 52期

基金：

美国国家科学基金会;

关键词：

D O I：

10.1021/ja806981k

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Full details are provided for the total synthesis of several members of the hapalindole family of natural products, including hapalindole Q, 12-epi-hapalindole D, 12-epi-fischerindole U, 12-epi-fischerindole G, 12-epi-fischerindole 1, and welwitindolinone A. Use of the recently developed direct indole coupling enabled an efficient, practical, scalable, and protecting-group-free synthesis of each of these natural products. The original biosynthetic proposal is reviewed, and a revised biosynthetic hypothesis is suggested, validated by the above syntheses. The syntheses are also characterized by an adherence to the concept of "redox economy". Analogous to "atom economy" or "step economy", "redox economy" minimizes the superfluous redox manipulations within a synthesis; rather, the oxidation state of intermediates linearly and steadily increases throughout the course of the synthesis.

引用

页码：17938 / 17954

页数：17

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