Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy
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 N-acyl oxazolidin-2-ones as key starting materials. The combination of the Evans aldol addition and the Prins cyclization allowed the diaster...
| Autores principales: | , , , , , , , |
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| Formato: | Articulo |
| Lenguaje: | Inglés |
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2018
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| Acceso en línea: | http://sedici.unlp.edu.ar/handle/10915/124083 |
| Aporte de: |
| id |
I19-R120-10915-124083 |
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| record_format |
dspace |
| institution |
Universidad Nacional de La Plata |
| institution_str |
I-19 |
| repository_str |
R-120 |
| collection |
SEDICI (UNLP) |
| language |
Inglés |
| topic |
Ciencias Exactas tetrahydropyrans alcohols Evans Aldol-Prins Strategy |
| spellingShingle |
Ciencias Exactas tetrahydropyrans alcohols Evans Aldol-Prins Strategy Álvarez Méndez, Sergio J. Fariña Ramos, Marta Villalba, María Luisa Perretti, Marcelle D. García, Celina Moujir, Laila Ramírez, Miguel A. Martín, Víctor S. Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy |
| topic_facet |
Ciencias Exactas tetrahydropyrans alcohols Evans Aldol-Prins Strategy |
| description |
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 N-acyl 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-step version, which additionally permitted the isolation of β,γ-unsaturated alcohol precursors 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 was performed for the preparation of a battery of more than 30 densely substituted tetrahydropyrans, unprecedentedly fused to a 1,3-oxazinane-2,4-dione ring, both in a racemic fashion and in an enantiomeric fashion. These novel molecules were successfully submitted to several transformations to permit 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 <i>Candida albicans</i>, and some structure-activity relationships were established. |
| format |
Articulo Articulo |
| author |
Álvarez Méndez, Sergio J. Fariña Ramos, Marta Villalba, María Luisa Perretti, Marcelle D. García, Celina Moujir, Laila Ramírez, Miguel A. Martín, Víctor S. |
| author_facet |
Álvarez Méndez, Sergio J. Fariña Ramos, Marta Villalba, María Luisa Perretti, Marcelle D. García, Celina Moujir, Laila Ramírez, Miguel A. Martín, Víctor S. |
| author_sort |
Álvarez Méndez, Sergio J. |
| title |
Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy |
| title_short |
Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy |
| title_full |
Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy |
| title_fullStr |
Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy |
| title_full_unstemmed |
Stereoselective Synthesis of Highly Substituted Tetrahydropyrans through an Evans Aldol-Prins Strategy |
| title_sort |
stereoselective synthesis of highly substituted tetrahydropyrans through an evans aldol-prins strategy |
| publishDate |
2018 |
| url |
http://sedici.unlp.edu.ar/handle/10915/124083 |
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Repositorios |
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1764820450759671809 |