Abstract
The high-pressure Diels-Alder reaction between 2,5-dimethylfuran and d-galacto-3,4,5,6,7-penta-O-acetyl-1,2-dideoxy-1-nitrohept-1-enitol led, after fractional crystallization from the crude product, to pure (2S,3R)-2-(endo-d-galacto-pentaacetoxypentyl)-1,4-dimethyl-3-exo-nitro-7-oxabicyclo[2.2.1]hept-5-ene. The structure was determined through a chemical route and by X-ray powder diffractometry. De-acetylation of the sugar side chain of this adduct caused the ring opening of the bicyclic system, followed by a tandem process of intramolecular nucleophilic additions, thus leading to new chiral bicyclic and tricyclic ethers.
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