A concise synthesis of alpha-amino acid N-carboxy anhydrides of (2S,3S)-beta-substituted serines

Authors
Palomo, C Oiarbide, M Ganboa, I Miranda, JI
Citation
C. Palomo et al., A concise synthesis of alpha-amino acid N-carboxy anhydrides of (2S,3S)-beta-substituted serines, TETRAHEDR L, 42(51), 2001, pp. 8955-8957
Citations number
17
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
51
Year of publication
2001
Pages
8955 - 8957
Database
ISI
SICI code
0040-4039(200112)42:51<8955:ACSOAA>2.0.ZU;2-F
Abstract
A general access to 3-hydroxy-4-(1-hydroxyalkyl)-beta -lactams with a C-4-C -1 relative configuration unlike is provided. The subsequent oxidative ring expansion of the corresponding 3-hydroxy beta -lactam smoothly affords an alpha -amino acid N-carboxy anhydride (NCA) formally derived from (2S,3S)-b eta -substituted serine, which upon sequential peptide coupling furnishes t he tripeptide segment 2, present in lysobactin. (C) 2001 Elsevier Science L td. All rights reserved.