Synlett 2012; 23(18): 2577-2581
DOI: 10.1055/s-0032-1317416
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© Georg Thieme Verlag Stuttgart · New York

Biomimetic Syntheses of the Flindersial Alkaloids

Ravikrishna Vallakati
Department of Chemistry, University of Houston, 136 Fleming Building, Houston, TX 77204-5003, USA   Fax: +1(713)7432709   Email: jmay@uh.edu
,
Jeremy A. May*
Department of Chemistry, University of Houston, 136 Fleming Building, Houston, TX 77204-5003, USA   Fax: +1(713)7432709   Email: jmay@uh.edu
› Author Affiliations
Further Information

Publication History

Received: 16 August 2012

Accepted after revision: 20 September 2012

Publication Date:
19 October 2012 (online)

Abstract

The flindersial alkaloids have a potentially novel mechanism for antimalarial activity. The recently disclosed flinderoles were postulated to be derived through dimerization of the natural product borrerine in a manner similar to their structural isomers, the borreverines. Recent work by the authors has shown that the flindersial alkaloids share a common biosynthetic origin to that of borrerine. The application of this insight has resulted in the synthesis of naturally occurring flindersial alkaloids with controlled formation of the structural isomer. Only three synthetic steps from tryptamine are needed for any of the natural products.

 
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