Synthetic approaches to the rigidin series of alkaloids employing vinylogous iminium salts

ORGN 617

John T. Gupton, jgupton@richmond.edu1, Edith J. Banner1, Stuart C. Clough1, Austin B. Scharf1, Bret R. Adams1, Barrett A. Little1, Jeffrey S. Moore, jsmoore@uiuc.edu2, and Itta Bluhn-Chertudi1. (1) Department of Chemistry, University of Richmond, 28 Westhampton Way, Richmond, VA 23173, (2) Department of Chemistry, University of Illinois, Urbana, IL 61801
Rigidin and its congeners are a class of alkaloids isolated from western Pacific marine tunicate species of the genus Eudistoma. These pyrrolo[2,3-d]pyrimidines have been shown to exhibit interesting biological activities, yet studies have been limited due to the scarcity of natural material. Efforts have been put forth to efficiently synthesize the Rigidin class of alkaloids for use in further biological evaluation. Our strategy involves the efficient preparation of a tetra-substituted pyrrole with functionality that can then be elaborated to form the pyrimidine ring. Due to the versatility of our pyrrole forming methodology several synthetic routes are accessible to attain the desired Rigidin compounds. The progress on the various routes will be presented.

 

Asymmetric Reactions, Heterocycles, Aromatics, Combinatorial, and Physical Organic Chemistry
8:00 PM-10:00 PM, Wednesday, 31 August 2005 Washington DC Convention Center -- Hall A, Poster

Division of Organic Chemistry

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