An approach to the synthesis of 5,5-trans-fused lactam analogues of beta-lactam antibiotics

Authors
Smith, PW Whittington, AR Cobley, KN Jaxa-Chamiec, A Finch, H
Citation
Pw. Smith et al., An approach to the synthesis of 5,5-trans-fused lactam analogues of beta-lactam antibiotics, J CHEM S P1, (1), 2001, pp. 21-25
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
14727781 → ACNP
Issue
1
Year of publication
2001
Pages
21 - 25
Database
ISI
SICI code
1472-7781(20010107):1<21:AATTSO>2.0.ZU;2-9
Abstract
A racemic synthesis of two diastereoisomeric alpha -benzyloxycarbonylamino substituted trans-fused bicyclic lactams (4 and 5), was achieved from cyclo pentene oxide. These lactams are useful intermediates to investigate the po ssibility of using a trans-lactam template as a replacement for the beta -l actam ring found in conventional antibacterial agents. One of the intermedi ates (4) was further elaborated to an analogue of the antibacterial agent c eftazidime.