Scalable total syntheses of (-)-hapalindole U and (+)-ambiguine H

TETRAHEDRON

卷:71

Article

Maimone, Thomas J.¹  Ishihara, Yoshihiro²  Baran, Phil S.² 

[1] Univ Calif Berkeley, Dept Chem, Berkeley, CA 94720 USA

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

关键词: Total synthesis;    Alkaloid;    Terpene;    Indole;    Protecting-group-free;   

DOI  :  10.1016/j.tet.2014.11.010

来源: Elsevier

【 摘 要 】

The Stigonemataceae family of cyanobacteria produces, a class of biogenetically related indole natural products that include hapalindoles and ambiguines. In this full account, a practical route to the tetracyclic hapalindole family is presented by way of an eight-step, enantiospecific, protecting-group-free total synthesis of (-)-hapalindole U that features an oxidative indole-enolate coupling. With gram-scale access to hapalindole U, the first total synthesis of an ambiguine alkaloid, (+)-ambiguine H, was cornpleted via an isonitrile-assisted prenyfation of an indole followed by a photofragmentation cascade. (C) 2014 Elsevier Ltd. All rights reserved.

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