A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis

Detalhes bibliográficos
Autor(a) principal: Castro,Fernando de Lima
Data de Publicação: 1999
Outros Autores: Kover,Renata Xavier, Kover,Warner Bruce, Jones Jr,Joel
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=S0103-50531999000200007
Resumo: This article presents the direct oxidation of limonene-oxide 1 with KIO4 in water, which is the best way to obtain the keto-aldehyde 3, an important intermediate in natural product synthesis. The cyclization of keto-aldehyde 3 with acidic Al2O3 proceeds chemoselectively to give ketone 4. These two reactions together increase the overall yield of ketone 4 to about 70% compared to 8% previously reported in the literature¹.
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spelling A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesisterpenoid chironsepoxide ring openingKIO4 oxidationchemoselective cyclizationThis article presents the direct oxidation of limonene-oxide 1 with KIO4 in water, which is the best way to obtain the keto-aldehyde 3, an important intermediate in natural product synthesis. The cyclization of keto-aldehyde 3 with acidic Al2O3 proceeds chemoselectively to give ketone 4. These two reactions together increase the overall yield of ketone 4 to about 70% compared to 8% previously reported in the literature¹.Sociedade Brasileira de Química1999-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531999000200007Journal of the Brazilian Chemical Society v.10 n.2 1999reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50531999000200007info:eu-repo/semantics/openAccessCastro,Fernando de LimaKover,Renata XavierKover,Warner BruceJones Jr,Joeleng2002-10-23T00:00:00Zoai:scielo:S0103-50531999000200007Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2002-10-23T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis
title A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis
spellingShingle A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis
Castro,Fernando de Lima
terpenoid chirons
epoxide ring opening
KIO4 oxidation
chemoselective cyclization
title_short A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis
title_full A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis
title_fullStr A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis
title_full_unstemmed A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis
title_sort A Novel Synthesis of 1-Acetyl-4-Isopropenyl-1-Cyclopentene by Chemoselective Cyclization of 4-Methyl-3-(Oxobutyl)-4-Pentenal: An Important Intermediate for Natural Product Synthesis
author Castro,Fernando de Lima
author_facet Castro,Fernando de Lima
Kover,Renata Xavier
Kover,Warner Bruce
Jones Jr,Joel
author_role author
author2 Kover,Renata Xavier
Kover,Warner Bruce
Jones Jr,Joel
author2_role author
author
author
dc.contributor.author.fl_str_mv Castro,Fernando de Lima
Kover,Renata Xavier
Kover,Warner Bruce
Jones Jr,Joel
dc.subject.por.fl_str_mv terpenoid chirons
epoxide ring opening
KIO4 oxidation
chemoselective cyclization
topic terpenoid chirons
epoxide ring opening
KIO4 oxidation
chemoselective cyclization
description This article presents the direct oxidation of limonene-oxide 1 with KIO4 in water, which is the best way to obtain the keto-aldehyde 3, an important intermediate in natural product synthesis. The cyclization of keto-aldehyde 3 with acidic Al2O3 proceeds chemoselectively to give ketone 4. These two reactions together increase the overall yield of ketone 4 to about 70% compared to 8% previously reported in the literature¹.
publishDate 1999
dc.date.none.fl_str_mv 1999-01-01
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=S0103-50531999000200007
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50531999000200007
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50531999000200007
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.10 n.2 1999
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
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