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 Wilkinsonʹs catalyst. Reduction and hydrogenation afforded carba-d-fructofuranose (2a).