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Biomimetic macrocycle-forming Diels-Alder reaction of an iminium dienophile: synthetic studies directed toward gymnodimine.
Johannes, Jeffrey W; Wenglowsky, Steve; Kishi, Yoshito.
Afiliação
  • Johannes JW; Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA.
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]
Assuntos
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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
Buscar no Google
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