New Conformationally Constrained Tryptophans by Nα-Cα-Cyclization to an Azetidin-2-one Core

Guillermo Gerona-Navarro; M. Angeles Bonache; Rosario Herranz; M. Teresa García-López; Rosario González-Muñiz

doi:10.1055/s-2000-7123

Synlett 2000; 2000(9): 1249-1252
DOI: 10.1055/s-2000-7123

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New Conformationally Constrained Tryptophans by N^α-C^α-Cyclization to an Azetidin-2-one Core

Guillermo Gerona-Navarro^* , M. Angeles Bonache, Rosario Herranz, M. Teresa García-López, Rosario González-Muñiz

^*Instituto de Química Médica (CSIC), Juan de la Cierva 3, 28006 Madrid, Spain; Fax +3 49 15 64 48 53; E-mail: iqmg313@iqm.csic.es

Abstract

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An entry to new conformationally restricted tryptophans, obtained through N^α-C^α-cyclization to an azetidin-2-one core, is described. The yield and ratio of β-lactamization from N^α-chloroacetyl tryptophan derivatives were dependent on the base and the solvent used. The chemoselective reduction of the β-lactam ring to the corresponding azetidine is also described.

constrained amino acids - azetidines/azetidin-2-ones - intramolecular alkylation - chemoselective reduction

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