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Synlett 1997; 1997(3): 289-290
DOI: 10.1055/s-1997-761
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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
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Publication History

Publication Date:
31 December 2000 (online)

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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