Studies directed toward the total synthesis of N-methylwelwitindolinone isothiocyanate

ORGN 28

James A. MacKay, mackayja@uchicago.edu1, Raynauld Bishop1, and Viresh H. Rawal, vrawal@uchicago.edu2. (1) Department of Chemistry, The University of Chicago, 5735 S. Ellis Ave, Chicago, IL 60637, (2) Department of Chemistry, University of Chicago, 5735 South Ellis Avenue, Chicago, IL 60637
In 1994, a new class of indole alkaloids was reported as isolated from the lipophilic extracts of both Hapalosiphon welwitschii and Westiella intricata. In the initial studies, the extracts from these cyanobacteria were found to have significant biological activities, including antifungal, larvacidal, and insecticidal properties. Significantly, the major component from each of these extracts, N-methylwelwitindolinone C isothiocyanate 1, was shown to reverse multidrug resistance (MDR) in chemotherapeutic treatment. We report herein an efficient, convergent synthesis of the core bicyclo[4.3.1]decane ring system of welwitindolinones in high overall yield starting from 4-bromindole.

 

Total Synthesis of Complex Molecules
8:00 AM-12:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- 202B, Oral

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005