Stereoselective synthesis of optically active 3-hydroxy-7,8-dihydro-beta-ionol-glucosides

A stereocontrolled synthesis of optically active beta-D-glucopyronosides 6a, b and 11a, b was accomplished via the 7,8-saturated alcohols 4a, b, efficiently prepared by an asymmetric transfer hydrogenation of the alpha,beta-acetylenic ketone 1 and subsequent catalytic hydrogenation. Simultaneous separation of these four glucosides by HPLC was also performed. This work is useful not only in order to confirm the stereochemistries of the trace amount of glucosides in plants but also to clarify their biosynthesis.