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

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.

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.

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

Referências bibliográficas

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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-373-373. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0373-1