Achmatowicz reaction
Organic synthesis
From Wikipedia, the free encyclopedia
The Achmatowicz reaction, also known as the Achmatowicz rearrangement or the Achmatowicz oxidation[1], is an organic synthesis in which a furan is converted to a dihydropyran. In the original publication by the Polish chemist Osman Achmatowicz Jr. (b. 20 December 1931 in Vilnius) in 1971 [2] 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 then ketone reduction with sodium borohydride produce an intermediate from which many monosaccharides can be synthesised.
| Achmatowicz reaction | |
|---|---|
| Named after | Osman Achmatowicz Jr. |
| Reaction type | Rearrangement reaction |
| Identifiers | |
| RSC ontology ID | RXNO:0000233 |
The Achmatowicz protocol has been used in total synthesis, including those of desoxoprosophylline,[3] pyrenophorin [4][5] Recently it has been used in diversity oriented synthesis[6][7]
and in enantiomeric scaffolding.[8][9]
