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We have developed an efficient methodology for the synthesis of (2 R ,3 S ,4 R )-2-hydroxymethyl-3,4-dihydroxy-6-aryl-7-aroylchromanes in which the chirality at the C -2, C -3, and C -4 positions is being drawn from C -glucopyranosyl aldehyde, which in turn can be efficiently synthesized from d-glucose. Thus, the synthesis starts with the transformation of sugar aldehyde into 1-( E -1-arylpropenon-3-yl)-3,4,6-tri- O -benzyl-d-glucals using Claisen-Schmidt type condensation reaction with different acetophenones and then to 1,2-disubstituted glucals via Pd(II)-catalyzed cross dehydrogenative coupling reaction, which in turn has been efficiently converted into (2 R ,3 S ,4 R )-chromanes via 6π-electrocyclization and in situ dehydrogenative aromatization.

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Synthesis and Structural Characterization of 1-(E-1-Arylpropenon-3-yl)-3,4,6-tri-O-benzyl-<scp>d</scp>-glucals and Their Transformation into Pentasubstituted (2R,3S,4R)-Chromanes via Pd-Catalyzed Cross Dehydrogenative Coupling Reaction

Synthesis and Structural Characterization of 1-(E-1-Arylpropenon-3-yl)-3,4,6-tri-O-benzyl-d-glucals and Their Transformation into Pentasubstituted (2R,3S,4R)-Chromanes via Pd-Catalyzed Cross Dehydrogenative Coupling Reaction