Iodomethyl Group as a Hydroxymethyl Synthetic Equivalent: Application to the Syntheses of <scp>d</scp>-<i>m</i><i>anno</i>-Hept-2-ulose and <scp>l</scp>-Fructose Derivatives

Abstract

The one-carbon elongation of aldoses to ketoses using iodomethyllithium as the key reagent in the homologation step is exemplified by the preparation of two carbohydrates of chemical and biological interests: d-manno-hept-2-ulose from d-mannose and l-fructose from l-arabinose.