SYNTHESIS OF 3-HYDROXYCEPHEMS FROM PENICILLIN-G THROUGH CYCLIZATION OF CHLORINATED 4-(PHENYLSULFONYLTHIO)-2-AZETIDINONES PROMOTED BY A BICL3 SN OR TICL4/SN BIMETAL REDOX SYSTEM/

Authors
TANAKA H TANIGUCHI M KAMEYAMA Y MONNIN M TORII S SASAOKA M SHIROI T NAGAO S YAMADA T TOKUMARU Y
Citation
H. Tanaka et al., SYNTHESIS OF 3-HYDROXYCEPHEMS FROM PENICILLIN-G THROUGH CYCLIZATION OF CHLORINATED 4-(PHENYLSULFONYLTHIO)-2-AZETIDINONES PROMOTED BY A BICL3 SN OR TICL4/SN BIMETAL REDOX SYSTEM/, Bulletin of the Chemical Society of Japan, 68(5), 1995, pp. 1385-1391
Citations number
20
Categorie Soggetti
Chemistry
Journal title
Bulletin of the Chemical Society of Japan → ACNP
ISSN journal
00092673
Volume
68
Issue
5
Year of publication
1995
Pages
1385 - 1391
Database
ISI
SICI code
0009-2673(1995)68:5<1385:SO3FPT>2.0.ZU;2-4
Abstract
A novel access to 3-hydroxycephems was attained from penicillin G via the C=C bond cleavage of -2-propenyl)-4-(phenylsulfonylthio)-2-azetidi nones by successive treatment with RuCl3/HIO4 and HIO4/CuSO4 and reduc tive cyclization of 1- 1-alkoxycarbonyl-3-chloro-2-hydroxy-1-propenyl) -4- (phenylsulfonylthio)-2-azetidinones on treatment with a newly devi sed BiCl3/Sn or TiCl4/Sn bimetal redox couple in DMF containing pyridi ne.