Collect. Czech. Chem. Commun.
2005, 70, 72-84
https://doi.org/10.1135/cccc20050072
Synthesis of β-D-Glucopyranosides of 6-Substituted 2-(Indol-3-yl)benzothiazoles
Martin Humeníka,*, Peter Kutschya, Katarína Valkováa, Branislav Horváthb, Vladimír Kováčikc and Slávka Bekešovác
a Institute of Chemical Sciences, Faculty of Science, P. J. Šafárik University, Moyzesova 11, 041 67 Košice, Slovak Republic
b Institute of Chemistry, Faculty of Science, Comenius University, Mlynská dolina CH-2, 842 15 Bratislava, Slovak Republic
c Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, 842 38 Bratislava, Slovak Republic
Abstract
A linear synthesis of substituted 1-(β-D-glucopyranosyl)benzocamalexins starting from indoline and penta-O-acetyl-β-D-glucopyranose was elaborated. Jacobson cyclization of corresponding 4-substituted peracetylated β-D-glucopyranosylindole-3-carbothioanilides employing potassium ferricyanide under basic conditions was a key synthetic step.
Keywords: Indoles; Jacobson reaction; Phytoalexins; Benzocamalexin; Glycosides; Glycosidations; Benzothiazoles; Thioamides; Nucleosides.
References: 46 live references.
