- 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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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.
- Afon'Kin,Kostrikin,Shumeiko,Popov,Matveev,Matvienko,Zabudkin
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p. 2149 - 2162
(2013/10/01)
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- Synthesis of taxoids 4. Novel and versatile methods for preparation of new taxoids by employing cis- or trans-phenyl glycidic acid
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A novel route to the synthesis of docetaxel using esterification of (2R,3R)-or (2R,3S)-glycidic acid with 7,10-bis-O-(2,2,2- trichloroethoxycarbonyl)-10-deacetylbaccatin III is described. Related novel taxoids which have new side chains were synthesized from these synthetic intermediates.
- Yamaguchi, Tetsuo,Harada, Naoyuki,Ozaki, Kunihiko,Hayashi, Masahito,Arakawa, Hiroaki,Hashiyama, Tomiki
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p. 1005 - 1016
(2007/10/03)
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