Synthesis, citotoxicity activity of new Cyclozonarone angular isomer

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.

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.

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

Referências bibliográficas

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Como citar:

Cuellar, M; Quiñones, N; Villena, J; Salas, C.; Espinoza, L.; "Synthesis, citotoxicity activity of new Cyclozonarone angular isomer", p-376-376. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0376-1