SYNTHESIS OF A 1-OXACEPHEM STRUCTURALLY RELATED TO CLAVULANIC ACID FROM D-GLUCURONOLACTONE

Authors
FURMAN B MOLOTOV S THURMER R KALUZA Z VOELTER W CHMIELEWSKI M
Citation
B. Furman et al., SYNTHESIS OF A 1-OXACEPHEM STRUCTURALLY RELATED TO CLAVULANIC ACID FROM D-GLUCURONOLACTONE, Tetrahedron, 53(16), 1997, pp. 5883-5890
Citations number
20
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
53
Issue
16
Year of publication
1997
Pages
5883 - 5890
Database
ISI
SICI code
0040-4020(1997)53:16<5883:SOA1SR>2.0.ZU;2-7
Abstract
[2+2]Cycloaddition of chlorosulfonyl isocyanate to 3-O-vinyl ethers de rived from D-glucose and D-glucuronolactone proceeded with an excellen t stereoselectivity to provide azetidin-2-ones with (R) configuration at C-4'. Intramolecular N-alkylation afforded 1-oxabicyclic-beta-lacta ms having six- or seven-membered ring fused to the four-membered one. (C) 1997 Elsevier Science Ltd.