Novel dioxabicyclic compound from L-fucose and malononitrile

CARB 50

Barbora Brazdova, b_brazdova@pacific.edu1, Pasit Phiasivongsa2, Paul H. Gross, vsamoshin@pacific.edu1, and Vyacheslav V. Samoshin, vsamoshin@pacific.edu1. (1) Department of Chemistry, University of the Pacific, 3601 Pacific Ave., Stockton, CA 95211, (2) SuperGen Inc, 4140 Dublin Blvd., Suite 200, Dublin, CA 94568
We explored a possibility of a C-glycoside synthesis starting with L-fucose 1 and malononitrile in the presence of a base catalyst. The reaction was much faster than the previously studied Henry condensation, and went further – to a double cyclization of 2:1 adduct into a novel dioxabicyclic compound 2. It provides a new route for the synthesis of chiral polysubstituted dihydropyrans and dihydrofurans.

 

General Posters
6:00 PM-8:00 PM, Tuesday, 28 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster

Division of Carbohydrate Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006