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Synlett 2001; 2001(6): 0773-0776
DOI: 10.1055/s-2001-14611
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Unusual Fused Tricyclic 2-Azetidinones: Stereocontrolled Synthesis of Rigid Dipeptide Surrogates from β-Lactam-Tethered Imines via Sequential Cycloaddition/Ring-Closing Metathesis

Benito Alcaide* , Pedro Almendros, Jose M. Alonso, Moustafa F. Aly, María C. Redondo
  • *Departamento de Química Orgánica I. Facultad de Química. Universidad Complutense 28040-Madrid, Spain; Fax + 34 91 39 44 103; E-mail: alcaide@eucmax.sim.ucm.es
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Publication Date:
31 December 2001 (online)

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The combination of [3 + 2] and [2 + 2]cycloaddition reactions of 2-azetidinone-tethered imines with ring-closing methatesis offers an asymmetric entry to a variety of unusual fused tricyclic 2-azetidinones bearing a bridgehead nitrogen atom, related to conformationally restricted peptidomimetics.

β-lactams - polycyclic amides - metathesis - peptidomimetics - asymmetric synthesis