aluno: brenno amaro dasilveira neto (pg) professor: aloir a. merlo remote asymmetric induction in an...
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Aluno: Brenno Amaro DaSilveira Neto (PG)Aluno: Brenno Amaro DaSilveira Neto (PG)
Professor: Aloir A. Merlo
Remote Asymmetric Induction in an Remote Asymmetric Induction in an Intramolecular Ionic Diels-Alder Reaction: Intramolecular Ionic Diels-Alder Reaction: Application to the Total Synthesis of (+)-Application to the Total Synthesis of (+)-
DihydrocompactinDihydrocompactin
Tarek Sammakia,* Deidre M. Johns, Ganghyeok Kim, and Martin A. BerlinerTarek Sammakia,* Deidre M. Johns, Ganghyeok Kim, and Martin A. Berliner
20052005, 127, 6504-6505
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INTRODUÇÃOINTRODUÇÃO
Os ácidos mevínicos constituem uma classe
importante de ácidos medicinais e são objetos de
inúmeros esforços sintéticos.
Dentre esses ácidos, encontra-se o (+)-
Dihidrocompactina.
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INTRODUÇÃOINTRODUÇÃO
H
H
O
Me
OO
OHO
(+)-Dihidrocompactina
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INTRODUÇÃOINTRODUÇÃO
(+)-Dihidrocompactina foi isolada como constituinte
minoritário da fermentação do Penicillium
brevicompactum.
Encontram-se na literatura relatados a síntese da
(+)-Dihidrocompactina sempre com o acoplamento de
fragmentos enantiomericamente enriquecidos, mas
nenhuma abordagem de indução a longa distância.
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ANÁLISE RETROSSINTÉTICAANÁLISE RETROSSINTÉTICA
H
H
O
Me
OO
OHO
(+) - Dihidrocompactina
H
H
O
Me
RHO
4
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ANÁLISE RETROSSINTÉTICAANÁLISE RETROSSINTÉTICA
H
H
O
Me
RHO
4
O
Me
RTMSO
1
2
+O
Me
R
3
H
H
O
Me
R
+
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Síntese do Aduto para Diels-AlderSíntese do Aduto para Diels-Alder
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Síntese do Aduto para Diels-AlderSíntese do Aduto para Diels-Alder
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Síntese do Aduto para Diels-AlderSíntese do Aduto para Diels-Alder
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Síntese do Aduto para Diels-AlderSíntese do Aduto para Diels-Alder
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Síntese do Aduto para Diels-AlderSíntese do Aduto para Diels-Alder
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Síntese do Aduto para Diels-AlderSíntese do Aduto para Diels-Alder
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Síntese do Aduto para Diels-AlderSíntese do Aduto para Diels-Alder
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A DIELS-ALDERA DIELS-ALDER
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A DIELS-ALDERA DIELS-ALDER
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A DIELS-ALDERA DIELS-ALDER
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A DIELS-ALDERA DIELS-ALDER
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A SínteseA Síntese
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A SínteseA Síntese
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ConclusãoConclusão
H
H
O
Me
OO
OHO
(+)-Dihidrocompactina
A reação de Diels-Alder como etapa chave e
controle a longa distância foi eficiente.