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dc.contributor.authorGarcía González, Celina Elena 
dc.contributor.authorÁlvarez Méndez, Sergio J.
dc.contributor.authorFariña Ramos, Marta
dc.contributor.authorVillalba, María Luisa
dc.contributor.authorPerretti, Marcelle D.
dc.contributor.authorMoujir, Laila M.
dc.contributor.authorRamírez, Miguel A. 
dc.contributor.authorMartín, Víctor S.
dc.date.accessioned2024-02-13T21:05:40Z
dc.date.available2024-02-13T21:05:40Z
dc.date.issued2018
dc.identifier.urihttp://riull.ull.es/xmlui/handle/915/36260
dc.description.abstractA direct and general method for the synthesis of naturally occurring 2,3,4,5,6- pentasubstituted tetrahydropyrans has been developed, employing β,γ-unsaturated Nacyl oxazolidin-2-ones as key starting materials. The combination of the Evans aldol addition and the Prins cyclization allowed the diastereoselective and efficient generation of the desired oxacycles in two fashions: a one-pot Evans aldol-Prins protocol, in which five new σ bonds and five contiguous stereocenters were straightforwardly generated, and a two-steps version, which additionally permitted the isolation of precursors β,γunsaturated alcohols bearing an N-acyl oxazolidin-2-one in the α position. From these alcohols were also obtained halogenated pentasubstituted tetrahydropyrans as well as 2,3,4,5-tetrasubstituted tetrahydrofurans, shedding light on the mechanism of the process. Computational studies were consistent with the experimental findings, and this innovative Evans aldol-Prins strategy conducted to the preparation of a battery of more than 30 densely substituted tetrahydropyrans, unprecedentedly fused to a 1,3-oxazinane2,4-dione ring, both in a racemic and in a enantiomeric fashion. These novel molecules were successfully submitted to several transformations to permit a simple access to a variety of differently functionalized tetrahydropyrans. Most of these unique molecules were evaluated for their antimicrobial activity against Gram-positive and Gram-negative bacteria and the yeast Candida albicans and some structure/activity relationships were established.en
dc.format.mimetypeapplication/pdf
dc.language.isoen
dc.relation.ispartofseriesThe Journal of Organic Chemistry, 83 (16), 2018
dc.rightsLicencia Creative Commons (Reconocimiento-No comercial-Sin obras derivadas 4.0 Internacional)
dc.rights.urihttps://creativecommons.org/licenses/by-nc-nd/4.0/deed.es_ES
dc.titleStereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy
dc.typeinfo:eu-repo/semantics/article
dc.identifier.doi10.1021/acs.joc.8b01182
dc.subject.keywordStereoselective Synthesis
dc.subject.keywordEvans Aldol−Prins Strategy
dc.subject.keywordTetrahydropyrans


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Licencia Creative Commons (Reconocimiento-No comercial-Sin obras derivadas 4.0 Internacional)
Except where otherwise noted, this item's license is described as Licencia Creative Commons (Reconocimiento-No comercial-Sin obras derivadas 4.0 Internacional)