STEREOSELECTIVE SYNTHESIS OF CIS-SUBSTITUTED AZETIDINONES FROM PENICILLIN - A FORMAL TOTAL SYNTHESIS OF LORACARBEF

Authors
DEETER JB HALL DA JORDAN CL JUSTICE RM KINNICK MD MORIN JM PASCHAL JW TERNANSKY RJ
Citation
Jb. Deeter et al., STEREOSELECTIVE SYNTHESIS OF CIS-SUBSTITUTED AZETIDINONES FROM PENICILLIN - A FORMAL TOTAL SYNTHESIS OF LORACARBEF, Tetrahedron letters, 34(19), 1993, pp. 3051-3054
Citations number
17
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
19
Year of publication
1993
Pages
3051 - 3054
Database
ISI
SICI code
0040-4039(1993)34:19<3051:SSOCAF>2.0.ZU;2-N
Abstract
A new method for the synthesis of chiral azetidinones bearing a carbon -carbon bond at the 4-position is described. The preparation involves a stereoselective alkylation-reduction of a silylated 4-phenylsulfonyl azetidinone. The utility of this method was demonstrated by a formal total synthesis of loracarbef.