Design, synthesis and biological evaluation of optically pure functionalized spiro[5,5]undecane-1,5,9-triones as HIV-1 inhibitors

Abstract

A single-step amino acid-catalyzed diastereoselective three-component synthesis of optically pure highly functionalized spiro[5,5]undecane-1,5,9- triones preferentially over the four stereoisomers was accomplished in very good yields with > 99% ee/de. Preliminary cell culture-based in vivo screening on these molecules revealed that cis-1aca and cis-1jca are better lead compounds for HIV-1 treatment than the known antiretroviral drug azidothymidine (AZT). © 2011 The Royal Society of Chemistry.