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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 s??ntese completa da mistura rac??mica do cyclozonarone ((??)-3), foi obtida a partir do E,E-farnesol (4) em uma seq????ncia de oito passos com um rendimento geral de 6,6%. O albicanol ((??)-1) e seu acetato ((??)-2) s??o intermedi??rios. Uma seq????ncia inicial, similar a partir do produto natural (-)-drimenol (5), produziu o(+)-albicanol (1) e o(+)-cyclozonarone (3) com 42% e 11%, respectivamente. A atividade citot??xica do composto(+)-cyclozonarone foi avaliada e mostrou alguma seletividade para MS-1 (c??lulas endoteliais de camundongos)

Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone