Efficient and Practical Asymmetric Synthesis of the Taxol C-13 Side Chain, N-Benzoyl-(2R,3S)-3-phenylisoserine, and Its Analogues via Chiral 3-Hydroxy-4-aryl-β-lactams through Chiral Ester Enolate–Imine Cyclocondensation

Iwao Ojima; Ivan Habus; Mangzhu Zhao; Gunda I. Georg; Lalith R. Jayasinghe

doi:10.1021/jo00005a003

Efficient and Practical Asymmetric Synthesis of the Taxol C-13 Side Chain, N-Benzoyl-(2R,3S)-3-phenylisoserine, and Its Analogues via Chiral 3-Hydroxy-4-aryl-β-lactams through Chiral Ester Enolate–Imine Cyclocondensation

Iwao Ojima
, Ivan Habus
, Mangzhu Zhao
, Gunda I. Georg
, Lalith R. Jayasinghe

Medicinal Chemistry

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

233 Scopus citations

Abstract

A highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with >96% ee is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogues.

Original language	English (US)
Pages (from-to)	1681-1683
Number of pages	3
Journal	Journal of Organic Chemistry
Volume	56
Issue number	5
DOIs	https://doi.org/10.1021/jo00005a003
State	Published - Mar 1 1991

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10.1021/jo00005a003

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Ojima, I., Habus, I., Zhao, M., Georg, G. I., & Jayasinghe, L. R. (1991). Efficient and Practical Asymmetric Synthesis of the Taxol C-13 Side Chain, N-Benzoyl-(2R,3S)-3-phenylisoserine, and Its Analogues via Chiral 3-Hydroxy-4-aryl-β-lactams through Chiral Ester Enolate–Imine Cyclocondensation. Journal of Organic Chemistry, 56(5), 1681-1683. https://doi.org/10.1021/jo00005a003

Efficient and Practical Asymmetric Synthesis of the Taxol C-13 Side Chain, N-Benzoyl-(2R,3S)-3-phenylisoserine, and Its Analogues via Chiral 3-Hydroxy-4-aryl-β-lactams through Chiral Ester Enolate–Imine Cyclocondensation. / Ojima, Iwao; Habus, Ivan; Zhao, Mangzhu et al.
In: Journal of Organic Chemistry, Vol. 56, No. 5, 01.03.1991, p. 1681-1683.

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

Ojima, I, Habus, I, Zhao, M, Georg, GI & Jayasinghe, LR 1991, 'Efficient and Practical Asymmetric Synthesis of the Taxol C-13 Side Chain, N-Benzoyl-(2R,3S)-3-phenylisoserine, and Its Analogues via Chiral 3-Hydroxy-4-aryl-β-lactams through Chiral Ester Enolate–Imine Cyclocondensation', Journal of Organic Chemistry, vol. 56, no. 5, pp. 1681-1683. https://doi.org/10.1021/jo00005a003

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abstract = "A highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with >96\% ee is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogues.",

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AB - A highly efficient chiral ester enolate-imine condensation giving 3-hydroxy-4-aryl-β-lactams with >96% ee is successfully applied to the asymmetric synthesis of the enantiomerically pure taxol C-13 side chain, N-benzoyl-(2R,3S)-3-phenylisoserine, and its analogues.

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Efficient and Practical Asymmetric Synthesis of the Taxol C-13 Side Chain, N-Benzoyl-(2R,3S)-3-phenylisoserine, and Its Analogues via Chiral 3-Hydroxy-4-aryl-β-lactams through Chiral Ester Enolate–Imine Cyclocondensation

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