A NOVEL PENTOSE SYNTHESIS VIA PALLADIUM(II)-CATALYZED CYCLIZATION OF AN UNSTABLE HEMIACETAL

[摘要]：PdCl2(PhCN)(2) (5 mol%)-catalyzed cyclization of a hemiacetal derived from (E,2S,3R)-2,3-isopropylidenedioxy-6-(tetrahydro-2H-pyran-2-yl)-4-hexena l and methanol gave substituted furanoside in moderate yield, exclusively via 5-exo-mode cyclization, without the need for a reoxidant. New stereogenic centers at C1 and C4 on the tetrahydrofuran ring showed preferential 1R and 4R stereochemistry due to anomeric effect (n(omicron)-sigma(c-omicron)*) and A(1,2) strain, respectively. This methodology was applied to stereocontrolled synthesis of pentoses: D-ribose and L-lyxose.

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