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

Detalhes bibliográficos
Autor(a) principal: Delgado,Virginia
Data de Publicação: 2008
Outros Autores: Armstrong,Veronica, Cortés,Manuel, Barrero,Alejandro F.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000700005
Resumo: 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).
id SBQ-2_50511550802940bdeac20a2464212804
oai_identifier_str oai:scielo:S0103-50532008000700005
network_acronym_str SBQ-2
network_name_str Journal of the Brazilian Chemical Society (Online)
repository_id_str
spelling Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonaronealbicanolalbicanyl acetatecyclozonaronetotal synthesischiral synthesisThe 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).Sociedade Brasileira de Química2008-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000700005Journal of the Brazilian Chemical Society v.19 n.7 2008reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532008000700005info:eu-repo/semantics/openAccessDelgado,VirginiaArmstrong,VeronicaCortés,ManuelBarrero,Alejandro F.eng2017-05-05T00:00:00Zoai:scielo:S0103-50532008000700005Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2017-05-05T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone
title Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone
spellingShingle Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone
Delgado,Virginia
albicanol
albicanyl acetate
cyclozonarone
total synthesis
chiral synthesis
title_short Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone
title_full Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone
title_fullStr Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone
title_full_unstemmed Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone
title_sort Synthesis of racemic and chiral albicanol, albicanyl acetate and cyclozonarone: cytotoxic activity of ent-cyclozonarone
author Delgado,Virginia
author_facet Delgado,Virginia
Armstrong,Veronica
Cortés,Manuel
Barrero,Alejandro F.
author_role author
author2 Armstrong,Veronica
Cortés,Manuel
Barrero,Alejandro F.
author2_role author
author
author
dc.contributor.author.fl_str_mv Delgado,Virginia
Armstrong,Veronica
Cortés,Manuel
Barrero,Alejandro F.
dc.subject.por.fl_str_mv albicanol
albicanyl acetate
cyclozonarone
total synthesis
chiral synthesis
topic albicanol
albicanyl acetate
cyclozonarone
total synthesis
chiral synthesis
description 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).
publishDate 2008
dc.date.none.fl_str_mv 2008-01-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000700005
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532008000700005
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532008000700005
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.19 n.7 2008
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
instacron:SBQ
instname_str Sociedade Brasileira de Química (SBQ)
instacron_str SBQ
institution SBQ
reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
repository.mail.fl_str_mv ||office@jbcs.sbq.org.br
_version_ 1750318169078104064

Registros relacionados