Total syntheses of (+)- and (-)-1,3,4,5-tetragalloylapiitol and revision of absolute configuration of naturally occurring (-)-1,3,4,5-tetragalloylapiitol

摘要

The total syntheses of (+)- and (-)-1,3,4,5-tetragalloylapiitol were achieved in seven steps from d- and l-ribose, respectively. By comparing the optical rotations of both enantiomers with those of the natural product, the absolute configuration at C-3 in the naturally occurring 1,3,4,5- tetragalloylapiitol has been revised to R. The absolute configurations at C-3 in the synthetic (+)- and (-)-1,3,4,5-tetragalloylapiitol were further confirmed by the circular dichroism exciton chirality method.