Document Detail

Chirospecific synthesis of spirocyclic beta-lactams and their characterization as potent type II beta-turn inducing peptide mimetics.
MedLine Citation:
PMID:  16388623     Owner:  NLM     Status:  MEDLINE    
[reaction: see text] Starting from natural proline, a practical chirospecific synthesis of spirocyclic beta-lactams of type 2 is described when a methylene moiety showing minimal steric demand is employed as a constraint element for adjusting the dihedral angle psi(i + 1). Employing the concept of self-reproduction of chirality, C-formylation of the oxazolidinone 5 afforded the key intermediate 7 taking advantage of an intermediate protection of the bridging element as a vinyl moiety. NMR- and IR-based conformational studies clearly indicated that spiro-beta-lactams of type 2 can serve as efficient beta-turn nucleators.
Holger Bittermann; Peter Gmeiner
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  71     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2006 Jan 
Date Detail:
Created Date:  2006-01-03     Completed Date:  2006-07-26     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  97-102     Citation Subset:  IM    
Department of Medicinal Chemistry, Emil Fischer Center, Friedrich Alexander University, Schuhstrasse 19, D-91052 Erlangen, Germany.
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MeSH Terms
Biomimetic Materials / chemical synthesis*,  chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Peptides / chemistry*
Spectrophotometry, Infrared
beta-Lactams / chemical synthesis,  chemistry*
Reg. No./Substance:
0/Peptides; 0/beta-Lactams

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