Asymmetric synthesis and biological activity of l-bicyclocarba-d4T

Abstract

Novel l-bicyclocarba-d4T (1), an enantiomer of d-N-MCd4T has been enantiopurely synthesized as a potent anti-HIV agent starting from (R)-epichlorohydrin using tandem alkylation, chemoselective reduction of ester in the presence of lactone functional group, Grignard reaction, RCM reaction, and Mitsunobu reaction as key steps. l-N-MCd4T (1) was found to be very potent anti-HIV-1 (EC50 = 6.76 μg/mL) agent with no cytotoxicity. Copyright © Taylor & Francis Group, LLC.