Chemoenzymatic Synthesis of alpha-Hydroxy-beta-methyl-gamma-hydroxy Esters: Role of the Keto-Enol Equilibrium To Control the Stereoselective Hydrogenation in a Key Step

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MetadadosDescriçãoIdioma
Autor(es): dc.contributorUniversidade Estadual Paulista (UNESP)-
Autor(es): dc.creatorMilagre, Cintia D. F.-
Autor(es): dc.creatorMilagre, Humberto M. S.-
Autor(es): dc.creatorMoran, Paulo J. S.-
Autor(es): dc.creatorRodrigues, J. Augusto R.-
Data de aceite: dc.date.accessioned2021-03-10T17:15:40Z-
Data de disponibilização: dc.date.available2021-03-10T17:15:40Z-
Data de envio: dc.date.issued2014-05-20-
Data de envio: dc.date.issued2014-05-20-
Data de envio: dc.date.issued2010-03-05-
Fonte completa do material: dc.identifierhttp://dx.doi.org/10.1021/jo902227f-
Fonte completa do material: dc.identifierhttp://hdl.handle.net/11449/20038-
Fonte: dc.identifier.urihttp://educapes.capes.gov.br/handle/11449/20038-
Descrição: dc.descriptionFundação de Amparo à Pesquisa do Estado de São Paulo (FAPESP)-
Descrição: dc.descriptionCoordenação de Aperfeiçoamento de Pessoal de Nível Superior (CAPES)-
Descrição: dc.descriptionConselho Nacional de Desenvolvimento Científico e Tecnológico (CNPq)-
Descrição: dc.descriptionFUNCAMP-UNICAMP-
Descrição: dc.descriptionalpha-Hydroxy-beta-methyl-gamma-hydroxy esters not only are found in many natural products and potent drugs but also are useful intermediates in organic synthesis due to their highly functionalized skeleton that can be further manipulated and applied in the synthesis of many compound with remarkable biological activities. This work was based on a chemoenzymatic approach to obtain these molecules with three contiguous stereogenic centers in a highly enantio- and diastereoselective way. Two distinct linear routes were proposed in which the key steps in both routes consisted of initial stereocontrolled ketoester bioreduction followed by unsaturated carbonyl bioreduction or reduction with Pd-C. Other key reactions in the synthesis include a Wasserman protocol for chain homologation and a Mannnich-type olefination with maintenance of enantiomeric excess for all intermediates during the sequence. Whereas route A gave exclusively the skeleton with 3R,4R,5S configuration (99% ee and 11.5% global yield after 7 steps), route B gave the skeleton with 3R,4R,5S and 3R,4S,5R configurations (dr 1:12, 98% ee and 20% global yield after 5 steps).-
Formato: dc.format1410-1418-
Idioma: dc.languageen-
Publicador: dc.publisherAmer Chemical Soc-
Relação: dc.relationJournal of Organic Chemistry-
Relação: dc.relation4.805-
Relação: dc.relation1,846-
Direitos: dc.rightsclosedAccess-
Título: dc.titleChemoenzymatic Synthesis of alpha-Hydroxy-beta-methyl-gamma-hydroxy Esters: Role of the Keto-Enol Equilibrium To Control the Stereoselective Hydrogenation in a Key Step-
Tipo de arquivo: dc.typelivro digital-
Aparece nas coleções:Repositório Institucional - Unesp

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