A highly enantioselective chemoenzymatic synthesis of syn-3-amino-2-hydroxy esters: key intermediates for taxol side chain and phenylnorstatine

dc.creatorRodrigues, JAR
dc.creatorMilagre, HMS
dc.creatorMilagre, CDF
dc.creatorMoran, PJS
dc.date2005
dc.dateSEP 19
dc.date2014-11-15T00:51:10Z
dc.date2015-11-26T16:09:12Z
dc.date2014-11-15T00:51:10Z
dc.date2015-11-26T16:09:12Z
dc.date.accessioned2018-03-28T22:57:48Z
dc.date.available2018-03-28T22:57:48Z
dc.identifierTetrahedron-asymmetry. Pergamon-elsevier Science Ltd, v. 16, n. 18, n. 3099, n. 3106, 2005.
dc.identifier0957-4166
dc.identifierWOS:000232242900016
dc.identifier10.1016/j.tetasy.2005.08.015
dc.identifierhttp://www.repositorio.unicamp.br/jspui/handle/REPOSIP/75902
dc.identifierhttp://www.repositorio.unicamp.br/handle/REPOSIP/75902
dc.identifierhttp://repositorio.unicamp.br/jspui/handle/REPOSIP/75902
dc.identifier.urihttp://repositorioslatinoamericanos.uchile.cl/handle/2250/1266558
dc.descriptionStarting from the bromination of alpha-ketoesters to obtain 3-bromo-2-oxoalkanoates and bioreduction with Saccharomyces cerevisiae entrapped in calcium alginate pellets with double gel layers, syn-(2R,3S)-beta-bromo-alpha-hydroxy esters were obtained regioselectively in high yields and high ee. These chiral bromohydrins were cyclized to epoxides that were transformed into oxazolidines and finally opened by acidic hydrolysis to give syn-(2S,3S)-beta-amino-alpha-hydroxy esters in high overall yields and high ee. The enantiomeric excesses of all the intermediates were maintained during the reaction sequence. (C) 2005 Elsevier Ltd. All rights reserved.
dc.description16
dc.description18
dc.description3099
dc.description3106
dc.languageen
dc.publisherPergamon-elsevier Science Ltd
dc.publisherOxford
dc.publisherInglaterra
dc.relationTetrahedron-asymmetry
dc.relationTetrahedron: Asymmetry
dc.rightsfechado
dc.rightshttp://www.elsevier.com/about/open-access/open-access-policies/article-posting-policy
dc.sourceWeb of Science
dc.subjectAlpha-keto Esters
dc.subjectBeta-amino Acids
dc.subjectBakers-yeast
dc.subjectStereoselective-synthesis
dc.subjectStereochemical Control
dc.subjectAsymmetric-synthesis
dc.subjectMicrobial Reduction
dc.subjectHydroxy Acids
dc.subjectDerivatives
dc.subjectInhibitors
dc.titleA highly enantioselective chemoenzymatic synthesis of syn-3-amino-2-hydroxy esters: key intermediates for taxol side chain and phenylnorstatine
dc.typeArtículos de revistas


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