Tetrahedron

Cyclodimerization by ring-closing metathesis: synthesis, computational, and biological evaluation of novel bis-azetidinyl-macrocycles

A Sliwa, G Dive, JLH Jiwan, J Marchand-Brynaert

Index: Sliwa, Aline; Dive, Georges; Habib Jiwan, Jean-Louis; Marchand-Brynaert, Jacqueline Tetrahedron, 2010 , vol. 66, # 49 p. 9519 - 9527

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Citation Number: 10

Abstract

During our research on novel, non-traditional, bicyclic β-lactams as potential inhibitors of Penicillin Binding Proteins (PBPs), we focused on the synthesis of 1, 3-bridged 2- azetidinones by RCM reaction from 1, 3-bis-ω-alkenoyl-3 (S)-amino-2-azetidinone precursors. Submitting the precursors to RCM, we faced an unexpected problem: cyclodimerization was the preferred outcome. This peculiar reactivity, explained by a ...