Hydroformylation of cyclopentenes, novel strategy for total synthesis of carba-D-fructofuranose

Carba-D-fructofuranose (2a) was synthesized in 3 steps from cyclopentene 3. Compound 3 was prepared in 90% yield from commercially available 2,3,5-tri-O-benzyl-D-arabinose. The C-5 hydroxylmethyl unit was incorporated into 3 via hydroformylation using Wilkinson's catalyst. Reduction and hydrogenation afforded carba-D-fructofuranose (2a). © 2002 Published by Elsevier Science Ltd.