Different roles of trifluoromethanesulfonyl chloride in the construction of heterocycles fused with beta-lactams

Authors
Hwu, JR Hakimelahi, S Lu, KL Tsay, SC
Citation
Jr. Hwu et al., Different roles of trifluoromethanesulfonyl chloride in the construction of heterocycles fused with beta-lactams, TETRAHEDRON, 55(26), 1999, pp. 8039-8044
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON
ISSN journal
00404020 → ACNP
Volume
55
Issue
26
Year of publication
1999
Pages
8039 - 8044
Database
ISI
SICI code
0040-4020(19990625)55:26<8039:DROTCI>2.0.ZU;2-X
Abstract
The cis-configurated tricyclic O-3-isooxacepham 5 and bicyclic isopenam 11 were synthesized. The key step for the preparation of 5 involves chlorinati on of the corresponding carbanion of 3 with CF3SO2Cl followed by an interna l alkylation. The biologically active isopenam II was synthesized from thio -S-ester 6 via intermediate 9. The key step involves chlorination of the th iol moiety in monocyclic beta-lactam 7 by CF3SO2Cl followed by an internal cyclization. (C) 1999 Elsevier Science Ltd. All rights reserved.