RT info:eu-repo/semantics/article
T1 Stereoselective Synthesis of Highly Substituted
Tetrahydropyrans through an Evans Aldol-Prins Strategy
A1 García González, Celina Elena
A1 Álvarez Méndez, Sergio J.
A1 Fariña Ramos, Marta
A1 Villalba, María Luisa
A1 Perretti, Marcelle D.
A1 Moujir, Laila M.
A1 Ramírez, Miguel A.
A1 Martín, Víctor S.
K1 Stereoselective Synthesis
K1 Evans Aldol−Prins Strategy
K1 Tetrahydropyrans
AB A 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 aldoladdition and the Prins cyclization allowed the diastereoselective and efficient generationof the desired oxacycles in two fashions: a one-pot Evans aldol-Prins protocol, in whichfive 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 thesealcohols were also obtained halogenated pentasubstituted tetrahydropyrans as well as2,3,4,5-tetrasubstituted tetrahydrofurans, shedding light on the mechanism of theprocess. Computational studies were consistent with the experimental findings, and thisinnovative Evans aldol-Prins strategy conducted to the preparation of a battery of morethan 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 moleculeswere successfully submitted to several transformations to permit a simple access to avariety of differently functionalized tetrahydropyrans. Most of these unique moleculeswere evaluated for their antimicrobial activity against Gram-positive and Gram-negativebacteria and the yeast Candida albicans and some structure/activity relationships wereestablished.
YR 2018
FD 2018
LK http://riull.ull.es/xmlui/handle/915/36260
UL http://riull.ull.es/xmlui/handle/915/36260
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DS Repositorio institucional de la Universidad de La Laguna
RD 10-may-2024