C-24 stereochemistry of marine Sterols: (22E)-24-Ethyl-24-methylcholesta-5,22-dien-3b-oβl and 24-Ethyl-24-methylcholest-5-en-3β-ol

Detalhes bibliográficos
Autor(a) principal: Echigo,Shizue
Data de Publicação: 2011
Outros Autores: Castellanos,Leonardo, Duque,Carmenza, Uekusa,Hidehiro, Hara,Noriyuki, Fujimoto,Yoshinori
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=S0103-50532011000500026
Resumo: The C-24 configurations of (22E)-24-ethyl-24-methylcholesta-5,22-dien-3β-ol (1) and 24-ethyl-24-methylcholest-5-en-3β-ol (2), isolated from the Colombian Caribbean sponge Topsentia ophiraphidites, were determined to be R and S, respectively, by comparing their NMR data with those of stereodefined (24R)- and (24S)-samples that were synthesized in routes involving the orthoester Claisen rearrangement of Δ23-22-allylic alcohols. This is the first synthetic study where the Claisen rearrangement is used to introduce a C-24 quaternary center in a stereospecific manner with acceptable yield. X-ray analysis of 1 confirmed these stereochemical assignments.
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spelling C-24 stereochemistry of marine Sterols: (22E)-24-Ethyl-24-methylcholesta-5,22-dien-3b-oβl and 24-Ethyl-24-methylcholest-5-en-3β-ol24-ethyl-24-methylcholesterol24-ethyl-24-methylcholesta-5,22-dien-3b-olTopsentia ophiraphiditesmarine sterolorthoester Claisen rearrangementThe C-24 configurations of (22E)-24-ethyl-24-methylcholesta-5,22-dien-3β-ol (1) and 24-ethyl-24-methylcholest-5-en-3β-ol (2), isolated from the Colombian Caribbean sponge Topsentia ophiraphidites, were determined to be R and S, respectively, by comparing their NMR data with those of stereodefined (24R)- and (24S)-samples that were synthesized in routes involving the orthoester Claisen rearrangement of Δ23-22-allylic alcohols. This is the first synthetic study where the Claisen rearrangement is used to introduce a C-24 quaternary center in a stereospecific manner with acceptable yield. X-ray analysis of 1 confirmed these stereochemical assignments.Sociedade Brasileira de Química2011-05-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011000500026Journal of the Brazilian Chemical Society v.22 n.5 2011reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532011000500026info:eu-repo/semantics/openAccessEchigo,ShizueCastellanos,LeonardoDuque,CarmenzaUekusa,HidehiroHara,NoriyukiFujimoto,Yoshinorieng2011-05-16T00:00:00Zoai:scielo:S0103-50532011000500026Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2011-05-16T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv C-24 stereochemistry of marine Sterols: (22E)-24-Ethyl-24-methylcholesta-5,22-dien-3b-oβl and 24-Ethyl-24-methylcholest-5-en-3β-ol
title C-24 stereochemistry of marine Sterols: (22E)-24-Ethyl-24-methylcholesta-5,22-dien-3b-oβl and 24-Ethyl-24-methylcholest-5-en-3β-ol
spellingShingle C-24 stereochemistry of marine Sterols: (22E)-24-Ethyl-24-methylcholesta-5,22-dien-3b-oβl and 24-Ethyl-24-methylcholest-5-en-3β-ol
Echigo,Shizue
24-ethyl-24-methylcholesterol
24-ethyl-24-methylcholesta-5,22-dien-3b-ol
Topsentia ophiraphidites
marine sterol
orthoester Claisen rearrangement
title_short C-24 stereochemistry of marine Sterols: (22E)-24-Ethyl-24-methylcholesta-5,22-dien-3b-oβl and 24-Ethyl-24-methylcholest-5-en-3β-ol
title_full C-24 stereochemistry of marine Sterols: (22E)-24-Ethyl-24-methylcholesta-5,22-dien-3b-oβl and 24-Ethyl-24-methylcholest-5-en-3β-ol
title_fullStr C-24 stereochemistry of marine Sterols: (22E)-24-Ethyl-24-methylcholesta-5,22-dien-3b-oβl and 24-Ethyl-24-methylcholest-5-en-3β-ol
title_full_unstemmed C-24 stereochemistry of marine Sterols: (22E)-24-Ethyl-24-methylcholesta-5,22-dien-3b-oβl and 24-Ethyl-24-methylcholest-5-en-3β-ol
title_sort C-24 stereochemistry of marine Sterols: (22E)-24-Ethyl-24-methylcholesta-5,22-dien-3b-oβl and 24-Ethyl-24-methylcholest-5-en-3β-ol
author Echigo,Shizue
author_facet Echigo,Shizue
Castellanos,Leonardo
Duque,Carmenza
Uekusa,Hidehiro
Hara,Noriyuki
Fujimoto,Yoshinori
author_role author
author2 Castellanos,Leonardo
Duque,Carmenza
Uekusa,Hidehiro
Hara,Noriyuki
Fujimoto,Yoshinori
author2_role author
author
author
author
author
dc.contributor.author.fl_str_mv Echigo,Shizue
Castellanos,Leonardo
Duque,Carmenza
Uekusa,Hidehiro
Hara,Noriyuki
Fujimoto,Yoshinori
dc.subject.por.fl_str_mv 24-ethyl-24-methylcholesterol
24-ethyl-24-methylcholesta-5,22-dien-3b-ol
Topsentia ophiraphidites
marine sterol
orthoester Claisen rearrangement
topic 24-ethyl-24-methylcholesterol
24-ethyl-24-methylcholesta-5,22-dien-3b-ol
Topsentia ophiraphidites
marine sterol
orthoester Claisen rearrangement
description The C-24 configurations of (22E)-24-ethyl-24-methylcholesta-5,22-dien-3β-ol (1) and 24-ethyl-24-methylcholest-5-en-3β-ol (2), isolated from the Colombian Caribbean sponge Topsentia ophiraphidites, were determined to be R and S, respectively, by comparing their NMR data with those of stereodefined (24R)- and (24S)-samples that were synthesized in routes involving the orthoester Claisen rearrangement of Δ23-22-allylic alcohols. This is the first synthetic study where the Claisen rearrangement is used to introduce a C-24 quaternary center in a stereospecific manner with acceptable yield. X-ray analysis of 1 confirmed these stereochemical assignments.
publishDate 2011
dc.date.none.fl_str_mv 2011-05-01
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=S0103-50532011000500026
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532011000500026
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532011000500026
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.22 n.5 2011
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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