Cycloadducts Synthesis and Relative Stereochemistry Determined by NMR and DFT-GIAO calculations

Cycloadducts Synthesis and Relative Stereochemistry Determined by NMR and DFT-GIAO calculations

Resende*, Gabriela da C.; Alvarenga, Elson S. de

Abstract:

The isobenzofuran-1(3H)-ones (or phthalides) and dihydro, tetrahydro, and hexahydro derivatives are a group of secondary metabolites mostly produced by several genera of the family Apiaceae. These bicyclic у-lactones have been studied because of their wide range of bioactivities.In our work, the Diels-Alder reaction was chosen as the key step to obtain tetrahydroisobenzofuran-1(3H)-ones derivatives from C-5 substituted butenolides, since ,-unsaturated -lactones act as excellent dienophiles in cycloaddition reactions with dienes.

The isobenzofuran-1(3H)-ones (or phthalides) and dihydro, tetrahydro, and hexahydro derivatives are a group of secondary metabolites mostly produced by several genera of the family Apiaceae. These bicyclic у-lactones have been studied because of their wide range of bioactivities.In our work, the Diels-Alder reaction was chosen as the key step to obtain tetrahydroisobenzofuran-1(3H)-ones derivatives from C-5 substituted butenolides, since ,-unsaturated -lactones act as excellent dienophiles in cycloaddition reactions with dienes.

Palavras-chave:

DOI: 10.5151/chempro-15bmos-BMOS2013_20139711943

Referências bibliográficas

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• [2] 2Chamoli,T.; Rawat, M. S. M. Med Chem. Res. 2013, 22, 453.
• [3] 3Benmeddah, A.; Mekelleche, S. M.; Benchouk, W.; Kara B. M.; Villemin, D. J. Mol.Struct.(Theochem).2007,821, 42.
• [4] 4 Ruano, J. L. G.; Bercial, F.; Fraile, A.; Castro, A. M. M.; Martín, M. R. Tetrahedron: Asymmetry.2000, 11, 4737.

Como citar:

Resende*, Gabriela da C.; Alvarenga, Elson S. de; "Cycloadducts Synthesis and Relative Stereochemistry Determined by NMR and DFT-GIAO calculations", p-23-23. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 2, Dezembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-15bmos-BMOS2013_20139711943