Biomimetic macrocycle-forming Diels-Alder reaction of an iminium dienophile: synthetic studies directed toward gymnodimine.
Org Lett
; 7(18): 3997-4000, 2005 Sep 01.
Article
em En
| MEDLINE
| ID: mdl-16119951
ABSTRACT
The macrocyclic core of gymnodimine has been constructed via an intramolecular Diels-Alder reaction of an alpha,beta-unsaturated iminium dienophile in water. The cycloaddition furnished a single exo-product, along with two endo-products. Through X-ray analysis of a suitable derivative, the stereochemistry of the exo-product was established, thereby demonstrating that its stereochemistry matches that of gymnodimine. In contrast, macrocyclization of an analogous alpha,beta-unsaturated ketone dienophile gave only undesired endo-products. Interestingly, the imine dienophile shows remarkable stability in water. [reaction see text]
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Compostos Heterocíclicos com 3 Anéis
/
Hidrocarbonetos Cíclicos
/
Iminas
Idioma:
En
Revista:
Org Lett
Assunto da revista:
BIOQUIMICA
Ano de publicação:
2005
Tipo de documento:
Article
País de afiliação:
Estados Unidos