title: Solid-Phase Synthesis of beta-Sultams.
abstract: Solid-phase synthesis of beta-sultams amenable for construction of sulfonyl beta-lactam analogue combinatorial libraries is reported. Imine intermediates generated from polymer-immobilized amino acids and aldehydes are reacted with (chlorosulfonyl)acetates in the presence of pyridine to afford the solid-phase-tethered beta-sultam products. The latter can be released from support by acidic cleavage (TFA) or photocleavage, depending on the nature of the linker employed (acid-labile or photolabile linkers). Immobilized 4-(9-fluorenyl)methoxycarbonyl beta-sultams are further functionalized on supports to afford, upon cleavage, the respective carboxy and amido thiazetidine derivatives. The method can be employed in production of beta-sultam libraries for identification of new antibacterial agents.
authors.affiliation: Affymax Research Institute, 3410 Central Expressway, Santa Clara, California 95051.
authors.forename: Mikhail F.
authors.initials: MF
authors.lastname: Gordeev
authors.forename: Eric M.
authors.initials: EM
authors.lastname: Gordon
authors.forename: Dinesh V.
authors.initials: DV
authors.lastname: Patel