Combined directed metalation and cross coupling tactics: A new carbanionic indole N-carbamoyl translocation reaction

ORGN 937

Victor Snieckus, snieckus@chem.queensu.ca1, Katherine A. Groom, katherine.groom@chem.queensu.ca2, and Zhongdong Zhao, zhongdongz@yahoo.ca2. (1) Department of Chemistry, Queen’s University, Chernoff Hall, 90 Bader Lane, Kingston, ON K7L 3N6, Canada, (2) Department of Chemistry, Queen's University, Chernoff Hall, 90 Bader Lane, Kingston, ON K7L 3N6, Canada
The biological and pharmaceutical activity of many indole alkaloids, including carbazole and indolocarbazole alkaloids isolated from natural sources, make them interesting target molecules for synthetic chemists. Recently, we discovered an indole N-CONEt2 to 2-aryl migration reaction under mild LDA-mediated conditions. The generalization of this reaction and preliminary results towards its application to total synthesis will be described.

 

Heterocycles and Aromatics
8:00 AM-12:00 PM, Thursday, August 23, 2007 BCEC -- 254 A/B, Oral

Division of Organic Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007