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

详细信息    查看全文

• 作者：Jeremy M. Richter ; Yoshihiro Ishihara ; Takeshi Masuda ; Brandon W. Whitefield ; Tomá ; s Llamas ; Antti Pohjakallio ; Phil S. Baran
• 刊名：Journal of the American Chemical Society
• 出版年：2008
• 出版时间：December 31, 2008
• 年：2008
• 卷：130
• 期：52
• 页码：17938-17954
• 全文大小：988K
• 年卷期：v.130,no.52(December 31, 2008)
• ISSN：1520-5126

文摘

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.