Study of the inversion reaction of the lactonic fusion on eremanthine derivatives
Autor(a) principal: | |
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Data de Publicação: | 2007 |
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=S0103-50532007000300023 |
Resumo: | The alpha-methylene-gamma-lactones 4(15)-dihydroeremanthine (8), 4(15),9(10)-tetrahydroeremanthine (9), isoeremanthine (10), allylic acetate delta1,10 (11), 1(R),10(R)-dihydromicheliolide (12) and 4alpha-hydroxy allylic acetate delta1,10 (13) were synthesized from the abundant natural product eremanthine (1). These substances were submitted to hydrolysis reaction with aqueous KOH and the carboxylic salts of these lactones had their hydroxy groups activated at the C-6 position by formation of respective mesylates (MsCl, Et3N, THF or DMSO) which underwent further displacement by carboxylate group. The utility of this methodology was investigated in order to obtain guaianolides with cis lactonic fusion at the C6-C7 position and to synthesize a precursor for posterior study of the biomimetic transformation of guaianolides into pseudoguaianolides. |
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Study of the inversion reaction of the lactonic fusion on eremanthine derivativeseremanthineinversion of configurationmolecular conformationThe alpha-methylene-gamma-lactones 4(15)-dihydroeremanthine (8), 4(15),9(10)-tetrahydroeremanthine (9), isoeremanthine (10), allylic acetate delta1,10 (11), 1(R),10(R)-dihydromicheliolide (12) and 4alpha-hydroxy allylic acetate delta1,10 (13) were synthesized from the abundant natural product eremanthine (1). These substances were submitted to hydrolysis reaction with aqueous KOH and the carboxylic salts of these lactones had their hydroxy groups activated at the C-6 position by formation of respective mesylates (MsCl, Et3N, THF or DMSO) which underwent further displacement by carboxylate group. The utility of this methodology was investigated in order to obtain guaianolides with cis lactonic fusion at the C6-C7 position and to synthesize a precursor for posterior study of the biomimetic transformation of guaianolides into pseudoguaianolides.Sociedade Brasileira de Química2007-01-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000300023Journal of the Brazilian Chemical Society v.18 n.3 2007reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.1590/S0103-50532007000300023info:eu-repo/semantics/openAccessAlves,José C. F.Fantini,Edna C.eng2007-06-28T00:00:00Zoai:scielo:S0103-50532007000300023Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2007-06-28T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false |
dc.title.none.fl_str_mv |
Study of the inversion reaction of the lactonic fusion on eremanthine derivatives |
title |
Study of the inversion reaction of the lactonic fusion on eremanthine derivatives |
spellingShingle |
Study of the inversion reaction of the lactonic fusion on eremanthine derivatives Alves,José C. F. eremanthine inversion of configuration molecular conformation |
title_short |
Study of the inversion reaction of the lactonic fusion on eremanthine derivatives |
title_full |
Study of the inversion reaction of the lactonic fusion on eremanthine derivatives |
title_fullStr |
Study of the inversion reaction of the lactonic fusion on eremanthine derivatives |
title_full_unstemmed |
Study of the inversion reaction of the lactonic fusion on eremanthine derivatives |
title_sort |
Study of the inversion reaction of the lactonic fusion on eremanthine derivatives |
author |
Alves,José C. F. |
author_facet |
Alves,José C. F. Fantini,Edna C. |
author_role |
author |
author2 |
Fantini,Edna C. |
author2_role |
author |
dc.contributor.author.fl_str_mv |
Alves,José C. F. Fantini,Edna C. |
dc.subject.por.fl_str_mv |
eremanthine inversion of configuration molecular conformation |
topic |
eremanthine inversion of configuration molecular conformation |
description |
The alpha-methylene-gamma-lactones 4(15)-dihydroeremanthine (8), 4(15),9(10)-tetrahydroeremanthine (9), isoeremanthine (10), allylic acetate delta1,10 (11), 1(R),10(R)-dihydromicheliolide (12) and 4alpha-hydroxy allylic acetate delta1,10 (13) were synthesized from the abundant natural product eremanthine (1). These substances were submitted to hydrolysis reaction with aqueous KOH and the carboxylic salts of these lactones had their hydroxy groups activated at the C-6 position by formation of respective mesylates (MsCl, Et3N, THF or DMSO) which underwent further displacement by carboxylate group. The utility of this methodology was investigated in order to obtain guaianolides with cis lactonic fusion at the C6-C7 position and to synthesize a precursor for posterior study of the biomimetic transformation of guaianolides into pseudoguaianolides. |
publishDate |
2007 |
dc.date.none.fl_str_mv |
2007-01-01 |
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=S0103-50532007000300023 |
url |
http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532007000300023 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
10.1590/S0103-50532007000300023 |
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.18 n.3 2007 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_ |
1750318168125997056 |