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Synlett 2013; 24(9): 1025-1031
DOI: 10.1055/s-0032-1318501
DOI: 10.1055/s-0032-1318501
synpacts
How to ‘Cope’ with the Prenylation of the Indole C4 Position
Authors
Further Information
Publication History
Received: 16 January 2013
Accepted after revision: 07 March 2013
Publication Date:
11 April 2013 (online)
Abstract
Evidence supporting an enzyme-catalyzed [3,3]-sigmatropic rearrangement of the dimethallylltryptophan synthase is highlighted. A bioinspired system is discussed, by which the chemical feasibility of Cope rearrangement to the 4-position of the indole nucleus was accomplished. Furthermore, synthesis of the tricyclic benzo[cd]indole core of welwitindolinones and dragmacidine E is presented.
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The structure of this intermediate is related to aza-Caisen rearrangements reported in:
For reviews, see:
For recent reviews, see:
Isolation of welwitindolinones:
For recent total syntheses of welwitindolinones, see: