Partial synthesis of 7a and 7b-hydroxy-ent-cyclozonarone and 7-hydroxy-chlorocyclozonarones derivatives

Partial synthesis of 7a and 7b-hydroxy-ent-cyclozonarone and 7-hydroxy-chlorocyclozonarones derivatives

Zelada, Jorge; Tapia, Ricardo; Cortés, Manuel; Armstrong, Veronica

Abstract:

Sesquiterpenquinone, cyclozonarone (1), isolated from Dictyopteris undulata, has proven antifeedant activity against abalones. The enantiomer of natural cyclozonarone ((+)-2) has shown activity against epimastigotes of Trypanosoma Cruzi, protozoo responsible for the Chagas disease. We have synthesized (+)- cyclozonarone (2) in a previous work. The important bioactivity of these sesquiterpenquinones aroused our interest in the synthesis of both epimers of 7- hydroxycyclozonarone (3 and 4) and chlorinated derivatives (5).

Sesquiterpenquinone, cyclozonarone (1), isolated from Dictyopteris undulata, has proven antifeedant activity against abalones. The enantiomer of natural cyclozonarone ((+)-2) has shown activity against epimastigotes of Trypanosoma Cruzi, protozoo responsible for the Chagas disease. We have synthesized (+)- cyclozonarone (2) in a previous work. The important bioactivity of these sesquiterpenquinones aroused our interest in the synthesis of both epimers of 7- hydroxycyclozonarone (3 and 4) and chlorinated derivatives (5).

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DOI: 10.5151/chempro-14bmos-R0119-1

Referências bibliográficas

• [1] 1 Kurata,T.;Taniguchi, K.; Suzuki, M. Phytochemistry, 1996,41, 749.
• [2] 2 Cuellar, M. A.; Salas,C.; Cortés, M. J.; Morello, A.; Maya, J.D.; Preite, M. D. Biorg. And Med. Chem.. 2003, 11, 2489.
• [3] 3 Cortés, M. ; Valderrama,J.; Cuellar, M. ; Armstrong, V.; Preite, M. D. J. Nat. Prod.. 2001, 64, 348.
• [4] 4 Appel, H.H.; Brooks, C.J.; Overton, K.H. J.Chem. Soc., 1959, 3322.

Como citar:

Zelada, Jorge; Tapia, Ricardo; Cortés, Manuel; Armstrong, Veronica; "Partial synthesis of 7a and 7b-hydroxy-ent-cyclozonarone and 7-hydroxy-chlorocyclozonarones derivatives", p-119-119. In: In Blucher Chemistry Proceedings, São Paulo, v. 1, n. 1, Setembro.2013. São Paulo: Blucher, 2013.
ISSN 23184043, DOI 10.5151/chempro-14bmos-R0119-1