Abstract
A retrospective account of a synthetic method development, which started as a study of a stepwise oxidative conversion of 2-furyl carbinols to pyranoses (Achmatowicz rearrangement) is presented. Application of most conceivable ways of stereo-differentiation of rearrangement substrates and products over the last 50 years rendered this simple transformation a unique position. Today it is one of the most versatile synthetic tools in synthesis of oxygen and nitrogen heterocyclic compounds, including a great variety of natural products. Evolution of rearrangement procedures which are environmentally friendly and secure firm control over stereochemistry of even most complex target molecules is highlighted. • The Achmatowicz rearrangement was a crucial step in a total synthesis of monosaccharides. • It transforms furyl carbinol into six-membered ring systems containing O or N atom. • There are dozens of conditions and reactants used to perform the rearrangement. • It is an exceptionally useful tool in total syntheses of pharmaceuticals, alkaloids, toxins, etc.
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