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

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Synthesis, citotoxicity activity of new Cyclozonarone angular isomer

Cuellar, M ; Quiñones, N ; Villena, J ; Salas, C. ; Espinoza, L. ;

Abstract:

Among the great variety of natural products, found in plants, algae and sea sponge, we can find compounds that have a quinonic/hydroquinonic moiety united to a terpenic skeleton. Natural (-)- cyclozonarone (1), is a drimanic benzoquinone derivative isolated from algae Dintyopteris undulata that posseses a powerful feeding-deterrant activity towards young abalones furthermore shows anticancer activity. The absolute configuration of 1 was establish through a six-step route, starting from natural (-) polygodial, leading us to the synthetic enantiomer (+)-cyclozonarone (2), that showed antileshmania activity. Later, (-)-cyclozonarone was synthesized starting from (+)-albicanol. Both routes of synthesis were based on the Diels-Alder reaction.

Abstract:

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Palavras-chave: ent-cyclozonarone, angular isomer, antitumoral activity,

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DOI: 10.5151/chempro-14bmos-R0376-1

Referências bibliográficas
  • [1] 1Kurata, K., Tanaguchi, K., Susuki, M.; Phytochem., 1996, 41, 749.
  • [2] 2 Curtis, M. D.; Shiu, K.; Butler, W. M. e Huffmann, J. C. J. Am. Chem. Soc. 1986, 108, 3335.
  • [3] 3 Cortés, M., Valderrama, J. A. Cuellar, M. Armstrong, V., Preite, M.; J. Nat. Prod., 2001, 64, 348.
  • [4] 4 Seifert, K., Schröder, J., Matthes, B. Tetrahedron Lett., 2001, 42, 8151.
  • [5] 5 Benites, J., Preite, M., Cortés, M.; Synth. Commun. 2001, 31 (9), 1347-1354.
Como citar:

Cuellar, M; Quiñones, N; Villena, J; Salas, C.; Espinoza, L.; "Synthesis, citotoxicity activity of new Cyclozonarone angular isomer", p. 376 . 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-R0376-1

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