Synthesis of Cyclic Pentadepsipeptoids Analogues of Sansalvamide A by Combination of Ugi and Passerini Reactions

Synthesis of Cyclic Pentadepsipeptoids Analogues of Sansalvamide A by Combination of Ugi and Passerini Reactions

Barreto, Angélica de Fátima S.; Vercillo, Otilie E.; Wessjohann, Ludger A.; Andrade, Carlos Kleber Z.

Abstract:

Sansalvamide A (San A, 1) is a natural product isolated from a marine fungus (Fussarium ssp.). This cyclic depsipeptide exhibits a potent anticarcinogenic activity on multiple cancer cell lines. In continuing our research on the synthesis of peptoids with potential pharmacological activity, we decided to perform the synthesis of cyclic depsipeptoids analogues of San A (2a-b, Figure 1) based on a strategy previously developed in our group, by combination of Ugi and Passerini reactions. To the best of our knowledge, the synthesis of cyclic depsipeptoids has not yet been explored.

Sansalvamide A (San A, 1) is a natural product isolated from a marine fungus (Fussarium ssp.). This cyclic depsipeptide exhibits a potent anticarcinogenic activity on multiple cancer cell lines. In continuing our research on the synthesis of peptoids with potential pharmacological activity, we decided to perform the synthesis of cyclic depsipeptoids analogues of San A (2a-b, Figure 1) based on a strategy previously developed in our group, by combination of Ugi and Passerini reactions. To the best of our knowledge, the synthesis of cyclic depsipeptoids has not yet been explored.

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DOI: 10.5151/chempro-14bmos-R0298-2

Referências bibliográficas

• [1] 1 (a) Belofskv, G. N.; Jensen, P. R.; Fenical, W. T. Tetrahedron Lett. 1999, 40, 2913; (b) Vasko, R. C.; Rodriguez, R. A.; Cunningham, C. N.; Ardi, V. C.; Agard, D. A.; McAlpine, S. R. ACS Med. Chem. Lett. 2010, 1, 4.
• [2] 2 (a) Vercillo, O. E.; Andrade, C. K. Z.; Wessjohann, L. A. Org. Lett. 2008, 10, 205. (b) Barreto, A .F. S.; Vercillo, O. E.; Birkett, M. A.; Caulfied, J. C.; Wessjohann, L. A.; Andrade, C. K. Z. Org. Biom. Chem. 2011, DOI:10.1039/C1OB05471F; (c) Barreto, A .F. S.; Vercillo, O. E.; Andrade, C. K. Z. J. Braz. Chem. Soc. 2011, 22, 462.

Como citar:

Barreto, Angélica de Fátima S.; Vercillo, Otilie E.; Wessjohann, Ludger A.; Andrade, Carlos Kleber Z.; "Synthesis of Cyclic Pentadepsipeptoids Analogues of Sansalvamide A by Combination of Ugi and Passerini Reactions", p-298-298. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0298-2