AN EFFICIENT SEMISYNTHESIS OF TAXOL FROM [(T-BUTYLDIMETHYLSILYL)OXY]-4-PHENYL-2-AZETIDINONE AND 7-(TRIETHYLSILYL)BACCATIN III

Authors
GEORG GI CHERUVALLATH ZS HARRIMAN GCB HEPPERLE M PARK H
Citation
Gi. Georg et al., AN EFFICIENT SEMISYNTHESIS OF TAXOL FROM [(T-BUTYLDIMETHYLSILYL)OXY]-4-PHENYL-2-AZETIDINONE AND 7-(TRIETHYLSILYL)BACCATIN III, Bioorganic & medicinal chemistry letters, 3(11), 1993, pp. 2467-2470
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
3
Issue
11
Year of publication
1993
Pages
2467 - 2470
Database
ISI
SICI code
0960-894X(1993)3:11<2467:AESOTF>2.0.ZU;2-Y
Abstract
An investigation of the ester enolate-imine cyclocondensation demonstr ated that (-)-10-dicyclohexylsulfamoyl-D-isoborneol is an excellent ch iral auxiliary for the formation of [(t-butyldimethylsilyl)oxy]-4-phen yl-2-azetidinone in high enantiomeric purity. Coupling between [(t-but yldimethylsilyl)oxy]-4-phenyl-2-azetidinone and 7-(triethylsilyl)bacca tin III in the presence of sodium hydride as the base provided an effi cient taxol semisynthesis.