Synlett 2013; 24(9): 1025-1031
DOI: 10.1055/s-0032-1318501
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© Georg Thieme Verlag Stuttgart · New York

How to ‘Cope’ with the Prenylation of the Indole C4 Position

Darius D. Schwarzer
Department of Chemistry, Institute of Organic Chemistry, Leibniz University of Hannover, Schneiderberg 1, 30167 Hannover, Germany   Fax: +43(511)7623011   Email: tanja.gaich@oci.uni-hannover.de
,
Philipp J. Gritsch
Department of Chemistry, Institute of Organic Chemistry, Leibniz University of Hannover, Schneiderberg 1, 30167 Hannover, Germany   Fax: +43(511)7623011   Email: tanja.gaich@oci.uni-hannover.de
,
Tanja Gaich*
Department of Chemistry, Institute of Organic Chemistry, Leibniz University of Hannover, Schneiderberg 1, 30167 Hannover, Germany   Fax: +43(511)7623011   Email: tanja.gaich@oci.uni-hannover.de
› Author Affiliations
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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