PDF herunterladen
Synlett 1997; 1997(3): 289-290
DOI: 10.1055/s-1997-761
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of Indole Phytoalexins Brassinin and Cyclobrassinin via [1-(tert-Butoxycarbonyl)indol-3-yl]-methyl Isothiocyanate as the Key Biomimetic Intermediate

Peter Kutschy1 , Ingrid Achbergerová2 , Milan Dzurilla2 , Mitsuo Takasugi3
  • 1Department of Organic Chemistry, Faculty of Natural Sciences, P.J. Šafárik University, Moyzesova 11, SK-04167 Košice, Slovak Republic, Fax 0042-95-6222124; E-mail kutschy@kosice.upjs.sk
  • 2Department of Organic Chemistry, Faculty of Natural Sciences, P.J. Šafárik University, Moyzesova 11, SK-04167 Košice, Slovak Republic
  • 3Division of Material Science, Graduate School of Environmental Earth Science, Hokkaido University, Sapporo 060, Japan
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

A four-step synthesis of 1-protected indol-3-ylmethyl isothiocyanates from indole-3-carboxaldehyde has been elaborated. [1-(tert-Butoxycarbonyl)indol-3-yl]-methyl isothiocyanate appeared to be a suitable biomimetic intermediate for the synthesis of protected phytoalexins brassinin and cyclobrassinin. Removing of the tert-butoxycarbonyl protecting group under specific conditions afforded phytoalexins identical with previously described compounds.

indole phytoalexins - brassinin - cyclobrassinin - isothiocyanate - biomimetic