Named after Osman Achmatowicz Jr. | Reaction type Rearrangement reaction | |
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The Achmatowicz reaction, also known as the Achmatowicz rearrangement, 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.
The Achmatowitz protocol has been used in total synthesis, including those of desoxoprosophylline, pyrenophorin and Bao Gong Teng A. Very recently it has been used in diversity oriented synthesis
and in enantiomeric scaffolding.