Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone Delgado, Virginia Armstrong, Verónica Cortés, Manuel Barrero, Alejandro F. Albicanol Abicanyl acetate Cyclozonarone Total synthesis Chiral synthesis 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). 2014-09-05T11:05:31Z 2014-09-05T11:05:31Z 2008 info:eu-repo/semantics/article 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] 0103-5053 http://hdl.handle.net/10481/32917 10.1590/S0103-50532008000700005 eng http://creativecommons.org/licenses/by-nc-nd/3.0/ info:eu-repo/semantics/openAccess Creative Commons Attribution-NonCommercial-NoDerivs 3.0 License Sociedade Brasileira de Química