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

doi:10.1016/S0960-894X(01)80979-3

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

Medicinal Chemistry

Research output: Contribution to journal › Article › peer-review

63 Scopus citations

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 language	English (US)
Pages (from-to)	2467-2470
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	3
Issue number	11
DOIs	https://doi.org/10.1016/S0960-894X(01)80979-3
State	Published - Nov 1993

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An efficient semisynthesis of taxol from (3R,4S)-N-Benzoyl-3-[(t-butyldimethylsilyl)oxy]-4-phenyl-2-azetidinone and 7-(Triethylsilyl)baccatin III. / Georg, Gunda I.; Cheruvallath, Zacharia S.; Harriman, Geraldine C.B. et al.
In: Bioorganic and Medicinal Chemistry Letters, Vol. 3, No. 11, 11.1993, p. 2467-2470.

Research output: Contribution to journal › Article › peer-review

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

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.",

author = "Georg, \{Gunda I.\} and Cheruvallath, \{Zacharia S.\} and Harriman, \{Geraldine C.B.\} and Michael Hepperle and Haeil Park",

year = "1993",

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doi = "10.1016/S0960-894X(01)80979-3",

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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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UR - https://www.scopus.com/pages/publications/0027724670#tab=citedBy

U2 - 10.1016/S0960-894X(01)80979-3

DO - 10.1016/S0960-894X(01)80979-3

M3 - Article

AN - SCOPUS:0027724670

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

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

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