The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone

Detalhes bibliográficos
Autor(a) principal: Brocksom,Timothy J.
Data de Publicação: 2006
Outros Autores: Brocksom,Ursula, Barbosa,Fernanda P.
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=S0103-50532006000400023
Resumo: (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone is synthesized from (R)-(-)-carvone by reduction and trialkylsilyl-enolether formation, cyclopropanation with methylene iodide and diethylzinc, followed by a Saegusa type oxidation with ferric chloride and finally dehydrochlorination with base. The title compound is obtained in five steps and 38% overall yield, being a useful chiron for guaiane sesquiterpene natural products.
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spelling The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenonecycloheptenonecarvonering expansionperhydroazuleneenantioselectivity(R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone is synthesized from (R)-(-)-carvone by reduction and trialkylsilyl-enolether formation, cyclopropanation with methylene iodide and diethylzinc, followed by a Saegusa type oxidation with ferric chloride and finally dehydrochlorination with base. The title compound is obtained in five steps and 38% overall yield, being a useful chiron for guaiane sesquiterpene natural products.Sociedade Brasileira de Química2006-08-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000400023Journal of the Brazilian Chemical Society v.17 n.4 2006reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532006000400023info:eu-repo/semantics/openAccessBrocksom,Timothy J.Brocksom,UrsulaBarbosa,Fernanda P.eng2006-08-25T00:00:00Zoai:scielo:S0103-50532006000400023Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2006-08-25T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone
title The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone
spellingShingle The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone
Brocksom,Timothy J.
cycloheptenone
carvone
ring expansion
perhydroazulene
enantioselectivity
title_short The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone
title_full The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone
title_fullStr The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone
title_full_unstemmed The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone
title_sort The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone
author Brocksom,Timothy J.
author_facet Brocksom,Timothy J.
Brocksom,Ursula
Barbosa,Fernanda P.
author_role author
author2 Brocksom,Ursula
Barbosa,Fernanda P.
author2_role author
author
dc.contributor.author.fl_str_mv Brocksom,Timothy J.
Brocksom,Ursula
Barbosa,Fernanda P.
dc.subject.por.fl_str_mv cycloheptenone
carvone
ring expansion
perhydroazulene
enantioselectivity
topic cycloheptenone
carvone
ring expansion
perhydroazulene
enantioselectivity
description (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone is synthesized from (R)-(-)-carvone by reduction and trialkylsilyl-enolether formation, cyclopropanation with methylene iodide and diethylzinc, followed by a Saegusa type oxidation with ferric chloride and finally dehydrochlorination with base. The title compound is obtained in five steps and 38% overall yield, being a useful chiron for guaiane sesquiterpene natural products.
publishDate 2006
dc.date.none.fl_str_mv 2006-08-01
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=S0103-50532006000400023
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532006000400023
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532006000400023
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.17 n.4 2006
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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