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Synthesis 2010(13): 2161-2170  
DOI: 10.1055/s-0029-1218811
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Study on the NBS-Induced Rearrangement of 2-tert-Prenyltryptamines

Santosh Kumar Adla, Gregor Golz, Peter G. Jones, Thomas Lindel*
Technische Universität Braunschweig, Institutes of Organic, Inorganic and Analytical Chemistry, Hagenring 30, 38106 Braunschweig, Germany
Fax: +49(531)3917744; e-Mail: th.lindel@tu-bs.de;
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Publication History

Received 20 April 2010
Publication Date:
02 June 2010 (online)

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Abstract

Treatment of 2-tert-prenyltryptamines with N-bromosuccinimide gives clean access to the marine natural product flustramine C and analogues with the tert-prenyl group shifted to the 3a-position of the resulting pyrrolo[2,3-b]indole (70-80%). Dihydroflustramine C was obtained by DIBAL-H reduction of flustramine C. Bromination or N-methylation of the indole moiety does not influence the course of the rearrangement.

Key words

alkaloids - flustramines - indole - marine natural products - prenyl migration

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Crystallographic data have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications No. CCDC 773395 (9), 773396 (12). Copies of the data can be obtained free of charge from www.ccdc.cam.ac.uk/data_request/cif.