TY - JOUR
T1 - An efficient semisynthesis of taxol from (3R,4S)-N-Benzoyl-3-[(t-butyldimethylsilyl)oxy]-4-phenyl-2-azetidinone and 7-(Triethylsilyl)baccatin III
AU - Georg, Gunda I.
AU - Cheruvallath, Zacharia S.
AU - Harriman, Geraldine C.B.
AU - Hepperle, Michael
AU - Park, Haeil
PY - 1993/11
Y1 - 1993/11
N2 - 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.
AB - 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.
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U2 - 10.1016/S0960-894X(01)80979-3
DO - 10.1016/S0960-894X(01)80979-3
M3 - Article
AN - SCOPUS:0027724670
SN - 0960-894X
VL - 3
SP - 2467
EP - 2470
JO - Bioorganic and Medicinal Chemistry Letters
JF - Bioorganic and Medicinal Chemistry Letters
IS - 11
ER -