Enantiospecific total synthesis of the hapalindoles, fischerindoles, and welwitindolinones via a redox economic approach

被引：0

作者：

Richter, Jeremy M. ^{[1
]}

Ishihara, Yoshihiro ^{[1
]}

Masuda, Takeshi ^{[1
]}

Whitefield, Brandon W. ^{[1
]}

Llamas, Tomás ^{[1
]}

Pohjakallio, Antti ^{[1
]}

Baran, Phil S. ^{[1
]}

机构：

[1] Department of Chemistry, Scripps Research Institute, 10550 North Torrey Pines Road, San Diego, CA 92037, United States

来源：

Journal of the American Chemical Society | 2008年 / 130卷 / 52期

关键词：

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 I; 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. © 2008 American Chemical Society;

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摘要：

Journal article (JA)

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页码：17938 / 17954