The enantioselective synthesis of (R)-(+)-6-isopropenyl-3-methyl-2-cycloheptenone
Autor(a) principal: | |
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Data de Publicação: | 2006 |
Outros Autores: | , |
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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Journal of the Brazilian Chemical Society (Online) |
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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 |
_version_ |
1750318167326982144 |