An efficient semisynthesis of taxol from (3R,4S)-N-Benzoyl-3-[(t-butyldimethylsilyl)oxy]-4-phenyl-2-azetidinone and 7-(Triethylsilyl)baccatin III

Gunda I. Georg, Zacharia S. Cheruvallath, Geraldine C.B. Harriman, Michael Hepperle, Haeil Park

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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.

Original languageEnglish (US)
Pages (from-to)2467-2470
Number of pages4
JournalBioorganic and Medicinal Chemistry Letters
Volume3
Issue number11
DOIs
StatePublished - Nov 1993

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