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Please use this identifier to cite or link to this item: http://hdl.handle.net/10481/32917

Title: Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone
Authors: Delgado, Virginia
Armstrong, Verónica
Cortés, Manuel
Barrero, Alejandro F.
Issue Date: 2008
Abstract: The total synthesis of racemic cyclozonarone ((±)-3) was achieved from E,E-farnesol (4) in an eight-step sequence in 6.6% overall yield. Albicanol ((±)-1) and its acetate ((±)-2) are intermediates. A similar sequence starting from natural (-)-drimenol (5) gave (+)-albicanol (1) and (+)-cyclozonarone (3) (42% and 11% yield, respectively). The cytotoxic activity of (+)-cyclozonarone was assayed and showed some selectivity towards MS-1 (mice endothelial cells).
A síntese completa da mistura racêmica do cyclozonarone ((±)-3), foi obtida a partir do E,E-farnesol (4) em uma seqüência de oito passos com um rendimento geral de 6,6%. O albicanol ((±)-1) e seu acetato ((±)-2) são intermediários. Uma seqüência inicial, similar a partir do produto natural (-)-drimenol (5), produziu o(+)-albicanol (1) e o(+)-cyclozonarone (3) com 42% e 11%, respectivamente. A atividade citotóxica do composto(+)-cyclozonarone foi avaliada e mostrou alguma seletividade para MS-1 (células endoteliais de camundongos).
Sponsorship: Authors are grateful to Dirección de Investigación y Postgrado, Facultad de Química, Pontificia Universidad Católica de Chile, for financial support, to MECESUP grant UCH 0116 de la Red Nacional de Doctorado en Química for HRMS analyses and to Dr. Luis Espinoza for valuable help with spectroscopic assignments.
Publisher: Sociedade Brasileira de Química
Keywords: Albicanol
Abicanyl acetate
Cyclozonarone
Total synthesis
Chiral synthesis
URI: http://hdl.handle.net/10481/32917
ISSN: 0103-5053
Rights : Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License
Citation: Delgado, V.; et al. Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone. Journal of the Brazilian Chemical Society, 19(7): 1258-1263 (2014). [http://hdl.handle.net/10481/32917]
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