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Synlett 2000; 2000(9): 1249-1252
DOI: 10.1055/s-2000-7123
DOI: 10.1055/s-2000-7123
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New Conformationally Constrained Tryptophans by Nα-Cα-Cyclization to an Azetidin-2-one Core
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Publication History
Publication Date:
31 December 2000 (online)
An entry to new conformationally restricted tryptophans, obtained through Nα-Cα-cyclization to an azetidin-2-one core, is described. The yield and ratio of β-lactamization from Nα-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