A stereoselective carbohydrate route to optically active furo[2,3-b]benzofuran ring system

A stereoselective synthesis of the furo[2,3-b] benzofuran ring system 8, commonly encountered in aflatoxins has been achieved by exploiting the inherent chirality of D-glucose. Ozonolysis of 4, followed by selective hydrolysis of the formate ester intermediate 6, yielded directly the target ring system 8, in good over all yields leading to the right stereochemistry at the ring junction corresponding to the naturally occurring isomer of aflatoxin.