Disclosed is a method of synthesizing new optically pure heterocyclic compounds using Pd(0) catalyzed intramolecular cyclizations. Analogs of cyclopentanes, like isoxazoline-2-oxide and furan, with similar framework to the cyclopentanes act as anti-HIV and anticancer agents which opens a whole new field for application of these compounds. Starting from a meso-diol, optically pure compounds were prepared without utilizing chiral ligands at any stage of the synthesis. The stereochemical outcome of the product (>99% ee) was influenced by desymmetrization catalyzed by Pseudomonas cepacia lipase and the stereo selective nature of the palladium catalyzed transformations.
Bisht, Kirpal S.; Van Olphen, Alberto; Khan, Pasha M.; and Bucher, Cynthia, "Antiviral activity of cyclopentene nitro-ester and derivatives" (2012). USF Patents. 365.
University of South Florida