Journal
TETRAHEDRON
Volume 71, Issue 22, Pages 3652-3665Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.11.010
Keywords
Total synthesis; Alkaloid; Terpene; Indole; Protecting-group-free
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Funding
- NIH/NIGMS [GM-071498]
- Arnold and Mabel Beckman Foundation
- Searle Scholarship Fund
- Sloan Foundation
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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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