Asymmetric synthesis of β-lactams and n-benzoyl-3-phenylisoserines via the staudinger reaction

Gunda I. Georg; Peter M. Mashava; Eyüp Akgün; Mark W. Milstead

doi:10.1016/S0040-4039(00)79708-5

Asymmetric synthesis of β-lactams and n-benzoyl-3-phenylisoserines via the staudinger reaction

Gunda I. Georg, Peter M. Mashava, Eyüp Akgün, Mark W. Milstead

Medicinal Chemistry

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Abstract

Reaction of benzaldimine 5 derived from 2,3,4,6-tetra-O-acetyl-β-D-galactoseamine with acid chloride 6 yields cis β-lactam 7 as a single diastereoisomer. Hydrolysis of β-lactam 7 followed by N-benzoylation provides access toward N-benzoyl (2S,3R)-3-phenylisoserine 9. N-Benzoyl-3-phenylisoserines are important building blocks for the semi-synthesis of the anti-cancer agent taxol.

Original language	English (US)
Pages (from-to)	3151-3154
Number of pages	4
Journal	Tetrahedron Letters
Volume	32
Issue number	27
DOIs	https://doi.org/10.1016/S0040-4039(00)79708-5
State	Published - Jul 1 1991

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title = "Asymmetric synthesis of β-lactams and n-benzoyl-3-phenylisoserines via the staudinger reaction",

abstract = "Reaction of benzaldimine 5 derived from 2,3,4,6-tetra-O-acetyl-β-D-galactoseamine with acid chloride 6 yields cis β-lactam 7 as a single diastereoisomer. Hydrolysis of β-lactam 7 followed by N-benzoylation provides access toward N-benzoyl (2S,3R)-3-phenylisoserine 9. N-Benzoyl-3-phenylisoserines are important building blocks for the semi-synthesis of the anti-cancer agent taxol.",

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AU - Georg, Gunda I.

AU - Mashava, Peter M.

AU - Akgün, Eyüp

AU - Milstead, Mark W.

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AB - Reaction of benzaldimine 5 derived from 2,3,4,6-tetra-O-acetyl-β-D-galactoseamine with acid chloride 6 yields cis β-lactam 7 as a single diastereoisomer. Hydrolysis of β-lactam 7 followed by N-benzoylation provides access toward N-benzoyl (2S,3R)-3-phenylisoserine 9. N-Benzoyl-3-phenylisoserines are important building blocks for the semi-synthesis of the anti-cancer agent taxol.

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JF - Tetrahedron Letters

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Asymmetric synthesis of β-lactams and n-benzoyl-3-phenylisoserines via the staudinger reaction

Abstract

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