Collect. Czech. Chem. Commun.
2005, 70, 487-506
https://doi.org/10.1135/cccc20050487
1,2-Anhydrosaccharides and 1,2-Cyclic Sulfites as Saccharide Donors in Convergent Synthesis of Glucopyranosyl-, Mannopyranosyl- and Ribofuranosylbenzocamalexin
Martin Humeníka,*, Peter Kutschya, Vladimír Kováčikb and Slávka Bekešováb
a Institute of Chemical Sciences, Faculty of Science, P. J. Šafárik University, Moyzesova 11, 041 67 Košice, Slovak Republic
b Institute of Chemistry, Slovak Academy of Sciences, Dúbravská cesta 9, 842 38 Bratislava, Slovak Republic
Abstract
A convergent synthesis of 1-(β-D-glucopyranosyl)-, 1-(α-D-mannopyranosyl)- and 1-(β-D-ribofuranosyl)benzocamalexin was elaborated as an alternative route to the linear approach based on the indoline-indole method. 1,2-Anhydrosaccharides and 1,2-cyclic sulfites as saccharide donors were used in the key glycosylation step. Coupling with benzocamalexin resulted in moderate to excellent yields of nucleoside analogs, depending on the saccharide donor, catalyst and solvent used.
Keywords: Indoles; Glycosides; Phytoalexins; Benzocamalexin; 1,2-Anhydrosacharides; Cyclic sulfites; Nucleosides; Glycosidations; Carbohydrates.
References: 80 live references.
