Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin

Detalhes bibliográficos
Autor(a) principal: Frederico,Daniel
Data de Publicação: 2009
Outros Autores: Constantino,Mauricio G., Donate,Paulo M.
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=S0103-50532009000500013
Resumo: The total synthesis of enantiomerically enriched (3S, 5R, 3'S, 5'R)-capsorubin (1) by aldol condensation of (1R, 4S)-1-(4-hydroxy-1,2,2-trimethyl-cyclopentyl) ethanone (2a) and crocetindial (3) is described. An alternative, short eight-step synthesis of the optically active compound 2a (ee 89%) is also reported.
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spelling Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubincarotenoidcapsorubincrocetindialcyclopentane keto-alkoholsynthesisThe total synthesis of enantiomerically enriched (3S, 5R, 3'S, 5'R)-capsorubin (1) by aldol condensation of (1R, 4S)-1-(4-hydroxy-1,2,2-trimethyl-cyclopentyl) ethanone (2a) and crocetindial (3) is described. An alternative, short eight-step synthesis of the optically active compound 2a (ee 89%) is also reported.Sociedade Brasileira de Química2009-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000500013Journal of the Brazilian Chemical Society v.20 n.5 2009reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532009000500013info:eu-repo/semantics/openAccessFrederico,DanielConstantino,Mauricio G.Donate,Paulo M.eng2009-06-29T00:00:00Zoai:scielo:S0103-50532009000500013Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2009-06-29T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin
title Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin
spellingShingle Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin
Frederico,Daniel
carotenoid
capsorubin
crocetindial
cyclopentane keto-alkohol
synthesis
title_short Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin
title_full Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin
title_fullStr Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin
title_full_unstemmed Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin
title_sort Total synthesis of (3S, 5R, 3'S, 5'R)-capsorubin
author Frederico,Daniel
author_facet Frederico,Daniel
Constantino,Mauricio G.
Donate,Paulo M.
author_role author
author2 Constantino,Mauricio G.
Donate,Paulo M.
author2_role author
author
dc.contributor.author.fl_str_mv Frederico,Daniel
Constantino,Mauricio G.
Donate,Paulo M.
dc.subject.por.fl_str_mv carotenoid
capsorubin
crocetindial
cyclopentane keto-alkohol
synthesis
topic carotenoid
capsorubin
crocetindial
cyclopentane keto-alkohol
synthesis
description The total synthesis of enantiomerically enriched (3S, 5R, 3'S, 5'R)-capsorubin (1) by aldol condensation of (1R, 4S)-1-(4-hydroxy-1,2,2-trimethyl-cyclopentyl) ethanone (2a) and crocetindial (3) is described. An alternative, short eight-step synthesis of the optically active compound 2a (ee 89%) is also reported.
publishDate 2009
dc.date.none.fl_str_mv 2009-01-01
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=S0103-50532009000500013
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532009000500013
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532009000500013
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.20 n.5 2009
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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