Achmatowicz reaction

Overview
The Achmatowicz Reaction is an organic synthesis in which a furan is converted to a dihydropyran. In the original publication by Osman Achmatowicz Jr. in 1971 furfuryl alcohol is reacted with bromine in methanol to 2,5-dimethoxy-2,5-dihydrofuran which rearranges to the dihydropyran with dilute sulfuric acid. Additional reaction steps, alcohol protection with methyl orthoformate and boron trifluoride) and ketone reduction with sodium borohydride produce an intermediate from which many monosaccharides can be synthesised.


 * [[Image:The Achmatowicz reaction.svg|600px|The Achmatowicz reaction]]

The Achmatowitz protocol has been used in total synthesis for example that of desoxoprosophylline, Pyrenophorin and Bao Gong Teng A. Very recently it has been used in diversity oriented synthesis


 * [[Image:AchmatowiczBurke2006.svg|600px|Achmatowicz Burke 2006]]

and in enantiomeric scaffolding.


 * [[Image:AchmatowiczReactionCoombs2008.svg|600px|Achmatowicz Reaction Coombs 2008]]