Solid-Phase Synthesis of β-Sultams

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Abstract
Solid-phase synthesis of β-sultams amenable for construction of sulfonyl β-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 β-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 β-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 β-sultam libraries for identification of new antibacterial agents.