Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G

Detalhes bibliográficos
Autor(a) principal: Santos,Leonardo S.
Data de Publicação: 2003
Outros Autores: Pilli,Ronaldo A.
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=S0103-50532003000600015
Resumo: The addition of 5-methyl-2-triisopropylsilyloxyfuran (5) to N-carbobenzyloxy-2-methoxypiperidine (6a) afforded a mixture of the corresponding erythro and threo isomers 7a and 8a, respectively, in moderate to good yields (42-85%) and diastereoisomeric ratio (7a : 8a) ranging from 1.1:1 _ 6:1 depending on the solvent system and the Lewis acid employed. The threo isomer 8a was eventually converted to (+/-)-homopumiliotoxin 223G (1) which was prepared in 5 steps and 13% overall yield from 6a.
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spelling Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223Ghomopumiliotoxin 223GN-acyliminium ionssilyloxyfuranvinylogous additionThe addition of 5-methyl-2-triisopropylsilyloxyfuran (5) to N-carbobenzyloxy-2-methoxypiperidine (6a) afforded a mixture of the corresponding erythro and threo isomers 7a and 8a, respectively, in moderate to good yields (42-85%) and diastereoisomeric ratio (7a : 8a) ranging from 1.1:1 _ 6:1 depending on the solvent system and the Lewis acid employed. The threo isomer 8a was eventually converted to (+/-)-homopumiliotoxin 223G (1) which was prepared in 5 steps and 13% overall yield from 6a.Sociedade Brasileira de Química2003-12-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600015Journal of the Brazilian Chemical Society v.14 n.6 2003reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532003000600015info:eu-repo/semantics/openAccessSantos,Leonardo S.Pilli,Ronaldo A.eng2004-02-11T00:00:00Zoai:scielo:S0103-50532003000600015Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2004-02-11T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G
title Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G
spellingShingle Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G
Santos,Leonardo S.
homopumiliotoxin 223G
N-acyliminium ions
silyloxyfuran
vinylogous addition
title_short Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G
title_full Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G
title_fullStr Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G
title_full_unstemmed Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G
title_sort Studies towards the construction of alkylidene quinolizidines: the total synthesis of homopumiliotoxin 223G
author Santos,Leonardo S.
author_facet Santos,Leonardo S.
Pilli,Ronaldo A.
author_role author
author2 Pilli,Ronaldo A.
author2_role author
dc.contributor.author.fl_str_mv Santos,Leonardo S.
Pilli,Ronaldo A.
dc.subject.por.fl_str_mv homopumiliotoxin 223G
N-acyliminium ions
silyloxyfuran
vinylogous addition
topic homopumiliotoxin 223G
N-acyliminium ions
silyloxyfuran
vinylogous addition
description The addition of 5-methyl-2-triisopropylsilyloxyfuran (5) to N-carbobenzyloxy-2-methoxypiperidine (6a) afforded a mixture of the corresponding erythro and threo isomers 7a and 8a, respectively, in moderate to good yields (42-85%) and diastereoisomeric ratio (7a : 8a) ranging from 1.1:1 _ 6:1 depending on the solvent system and the Lewis acid employed. The threo isomer 8a was eventually converted to (+/-)-homopumiliotoxin 223G (1) which was prepared in 5 steps and 13% overall yield from 6a.
publishDate 2003
dc.date.none.fl_str_mv 2003-12-01
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=S0103-50532003000600015
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532003000600015
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.1590/S0103-50532003000600015
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.14 n.6 2003
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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