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Regio- and stereoselective methods for the conversion of (2S,3R)-β-phenylglycidic acid esters to taxoids and other enantiopure (2R,3S)-phenylisoserine esters

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Abstract

A novel efficient method was proposed for the synthesis of enantiopure precursors of taxane-containing cytostatics, i.e., methyl esters of (2R,3S)- and (2S,3R)-N-benzoylphenylisoserine and similar taxoid esters. The method is based on the regio- and stereoselective hydrobromolysis of the corresponding trans-β-phenyl glycidate enatiomers, consecutive reactions of O-acylcarbamoylation of the obtained 3-bromohydrins, intramolecular cyclization to 4-phenyloxazolidin-2-one-5-carboxylic acid derivatives, and oxazolidinone ring opening.

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  1. L. M. Litvinenko Institute of Physicoorganic Chemistry and Coal Chemistry, National Academy of Sciences of Ukraine, 70 ul. R. Lyuksemburg, 83114, Donetsk, Ukraine

    A. A. Afon’kin, L. M. Kostrikin, A. E. Shumeiko, A. F. Popov & A. A. Matveev

  2. Co. Ltd “Sinbias Farma,”, 181 ul. Krepil’shchikov, 83085, Donetsk, Ukraine

    A. A. Afon’kin, A. A. Matveev, V. N. Matvienko & A. F. Zabudkin

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  1. A. A. Afon’kin
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  2. L. M. Kostrikin
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Correspondence to A. A. Afon’kin.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2132–2145, November, 2012.

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Afon’kin, A.A., Kostrikin, L.M., Shumeiko, A.E. et al. Regio- and stereoselective methods for the conversion of (2S,3R)-β-phenylglycidic acid esters to taxoids and other enantiopure (2R,3S)-phenylisoserine esters. Russ Chem Bull 61, 2149–2162 (2012). https://doi.org/10.1007/s11172-012-0302-4

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