New conformationally constrained tryptophans by N-alpha-C-alpha-cyclization to an azetidin-2-one core

Authors
Gerona-Navarro, G Bonache, MA Herranz, R Garcia-Lopez, MT Gonzalez-Muniz, R
Citation
G. Gerona-navarro et al., New conformationally constrained tryptophans by N-alpha-C-alpha-cyclization to an azetidin-2-one core, SYNLETT, (9), 2000, pp. 1249-1252
Citations number
29
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
SYNLETT
ISSN journal
09365214 → ACNP
Issue
9
Year of publication
2000
Pages
1249 - 1252
Database
ISI
SICI code
0936-5214(200009):9<1249:NCCTBN>2.0.ZU;2-5
Abstract
An entry to new conformationally restricted tryptophans, obtained through N -alpha-C-alpha-cyclization to an azetidin-2one core, is described. The yiel d and ratio of beta -lactamization from N-alpha-chloroacetyl tryptophan der ivatives were dependent on the base and the solvent used. The chemoselectiv e reduction of the beta -lactam ring to the corresponding azetidine is also described.