Progress toward the synthesis of cis-2,3-epoxy-5-phenylpentan-1-ol derivatives, precursors to potential HIV-1 protease inhibitors

ORGN 161

Matthew R. Dintzner, mdintzne@depaul.edu, Thomas W. Lyons, tlyons@depaul.edu, Michael H. Akroush, mikeakroush@yahoo.com, and Paul Wucka, Fozziebear320@aol.com. Department of Chemistry, DePaul University, 1036 West Belden Avenue, Chicago, IL 60614
A novel synthetic route to a series of cis-2,3-epoxy-5-phenylpentan-1-ols (1) is described. The target compounds (1), which are precursors to potential HIV-1 protease inhibitors, are generated from the corresponding cis-allylic alcohols (2) via Sharpless asymmetric epoxidation (SAE). The novel features of our synthetic scheme include clay-catalyzed, microwave-assisted (MWI) hetero-Diels Alder reaction of 2,3-dimethyl-1,3-butadiene with benzaldehyde derivatives to give benzopyrans (3) and subsequent Birch reduction to afford the corresponding cis-allylic alchols (2), exclusively.

 

Heterocycles, Aromatics, Materials, Devices, Switches, Combinatorial Chemistry, Metal-Mediated Reactions
8:00 PM-10:00 PM, Sunday, 13 March 2005 Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 229th ACS National Meeting, in San Diego, CA, March 13-17, 2005