title: Quasi-Biomimetic Ring Contraction Catalyzed by a Cysteine-Based Nucleophile: Total Synthesis of Sch-642305, Some Analogs and their Putative anti-HIV Activities.
abstract: Cysteine plays a number of important functional and structural roles in Nature, often in the realm of catalysis. Herein, we present an example of a cysteine-catalyzed Rauhut-Currier reaction for a potentially biomimetic synthesis of Sch-642305 and related analogs. In this key step of the synthesis we discuss interesting new discoveries and the importance of substrate-catalyst recognition, as well as cysteine's structural features. Also, we investigate the activity of Sch-642305 and four analogs in HIV-infected T-cells.
authors.affiliation: Department of Chemistry, Yale University, 225 Prospect Street, New Haven, CT 06520 -8107 (USA).
authors.forename: Alpay
authors.initials: A
authors.lastname: Dermenci
authors.forename: Philipp S
authors.initials: PS
authors.lastname: Selig
authors.forename: Robert A
authors.initials: RA
authors.lastname: Domaoal
authors.forename: Krasimir A
authors.initials: KA
authors.lastname: Spasov
authors.forename: Karen S
authors.initials: KS
authors.lastname: Anderson
authors.forename: Scott J
authors.initials: SJ
authors.lastname: Miller