Gunda Ingrid Georg, Z. Cheruvallath, G. Harriman
Nov 1, 1993
Citations
0
Influential Citations
29
Citations
Journal
Bioorganic & Medicinal Chemistry Letters
Abstract
Abstract An investigation of the ester enolate-imine cyclocondensation demonstrated that (−)-10-dicyclohexylsulfamoyl-D-isoborneol is an excellent chiral auxiliary for the formation of (3R,4S)-3-[(t-butyldimethylsilyl)oxy]-4-phenyl-2-azetidinone in high enantiomeric purity. Coupling between (3R,4S)-N-benzoyl-3-[(t-butyldimethylsilyl)oxy]-4-phenyl-2-azetidinone and 7-(triethylsilyl)baccatin III in the presence of sodium hydride as the base provided an efficient taxol semisynthesis.