Setembro 2013 vol. 1 num. 1 - Brazilian Meeting on Organic Synthesis 2011

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Stereoselective synthesis of β,γ-cis-β -acyl- γ- hydroxymethylene-butyrolactones via chiral nitroalkanes

Barreto, Silvana Constantino Rocha ; Junior, Cleber Bomfim Barreto ; Pereira, Vera Lúcia Patrocínio ;

Abstract:

Butyrolactones make part of a class of substances with high occurrence in nature. They have different biological profile such as potent antibiotics, antivirals, antifungal among others. Because of these important biological activities various synthetic methodologies capable of producing the butyrolactone ring β,γ-disubstituted are available in literature, however, few methods allow the introduction of the cis relative stereochemistry between C3-C4 and an acyl group at position C3 . This study aims to develop a new synthetic route to obtain enantiopure cis β,γ-disubstituted γ-butyrolactone rings, using nitroalkanes as nucleophiles in diastereoselective Michael additions.

Abstract:

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Palavras-chave: Michael addition, chiron approach, stereoselective synthesis,

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DOI: 10.5151/chempro-14bmos-R0373-1

Referências bibliográficas
  • [1] Huneck, S. Fortschr.Chem.Org.Naturst. 2001, 81, 1-276.
  • [2] Seitz, M.; Reiser, O. Current Opinion in Chemical Biology 2005, 9, 285-29
  • [3] Dias, L. C.; de Castro, I. B. D.; Steil, L. J.; Augusto, T. Tetrahedron Lett. 2006, 47, 213-216.
  • [4] Donate, P. M.; Frederico, D.; da Silva, R.; Constantino, M. G.; Del Ponte,G.; Bonatto, P. S. Tetrahedron-Asymmetry 2003, 14, 3253-3256.
  • [5] Gissot, A.; N'Gouela, S.; Matt, C.; Wagner, A.; Mioskowski, C. J.Org.Chem. 2004, 69, 8997-9001.
  • [6] Barreto-Junior, C. B.; Pereira, V. L. P. Tetrahedron Lett. 2009, 50, 6389- 6392
Como citar:

Barreto, Silvana Constantino Rocha; Junior, Cleber Bomfim Barreto; Pereira, Vera Lúcia Patrocínio; "Stereoselective synthesis of β,γ-cis-β -acyl- γ- hydroxymethylene-butyrolactones via chiral nitroalkanes", p. 373 . In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 2318-4043, DOI 10.5151/chempro-14bmos-R0373-1

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