An expeditious approach to (+)-polyoxamic acid and derivatives from asymmetric Morita-Baylis-Hillman reaction.

An expeditious approach to (+)-polyoxamic acid and derivatives from asymmetric Morita-Baylis-Hillman reaction.

Guidotti, Bruno Boni; Correia, José Tiago Menezes; Ullah, Hamid; Coelho., Fernando Antônio Santos

Abstract:

Polyoxins are natural nucleoside peptides isolated from strains of Streptomyces cacoi var. asoensis which present a relevant antifungal activity by inhibition of chitin synthase. The preparation of polyoxins is focused on the synthesis of the α-amino acid portion, (+)-polyoxamic acid, since the synthesis of its nucleoside residue is well described in literature. The purpose of this work is to propose a new approach to the synthesis of (+)-polyoxamic acid and derivatives starting from an asymmetric Morita-Baylis-Hillman (MBH) reaction. The antibacterial profile of these derivatives will be also evaluated.

Polyoxins are natural nucleoside peptides isolated from strains of Streptomyces cacoi var. asoensis which present a relevant antifungal activity by inhibition of chitin synthase. The preparation of polyoxins is focused on the synthesis of the α-amino acid portion, (+)-polyoxamic acid, since the synthesis of its nucleoside residue is well described in literature. The purpose of this work is to propose a new approach to the synthesis of (+)-polyoxamic acid and derivatives starting from an asymmetric Morita-Baylis-Hillman (MBH) reaction. The antibacterial profile of these derivatives will be also evaluated.

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DOI: 10.5151/chempro-15bmos-BMOS2013_2013820193928

Referências bibliográficas

• [1] 1 Isono, K.; Asahi, A.; Suzuki, S. J. Am. Chem. Soc. 1969, 91, 7490-7505.
• [2] 2 Porto, R. S., Amarante, G. W., Cavallaro, M., Poppi, R. J.,
• [3] Coelho, F. Tetrahedron Letters, 2009, 50, 1184-1187.

Como citar:

Guidotti, Bruno Boni; Correia, José Tiago Menezes; Ullah, Hamid; Coelho., Fernando Antônio Santos; "An expeditious approach to (+)-polyoxamic acid and derivatives from asymmetric Morita-Baylis-Hillman reaction.", p-190-190. 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_2013820193928