Journal of the Chemical Society Chemical Communications · 1992 · 11 citations · 2 references
Natural SciencesChemistryCarbohydrate BiochemistryCarbohydrate ChemistryCarbohydrate SynthesisHeterocyclic ChemistryMonosaccharide ChemistryRetrosynthetic Analysis[2+2] Cycloaddition[4+2] CycloadditionCycloaddition ReactionsOligosaccharide SynthesisStereochemistry Of Sugar DerivativesStereoselective Sugar SynthesisSugar IsomerizationSugar Ring Formation
Cyclopentadiene reacts with a D-glucose-derived hex-3-enose derivative to give norbornene derivatives attached at the 2,3-position of a 1,6-anhydrohexose skeleton; although the bicyclic enone isolevoglucosenone is a plausible intermediate in this reaction, the products actually appear to arise through initial cycloaddition to a rearranged acyclic sugar derivative with subsequent generation of the anhydro ring.
2
Synthesis and thermal chemistry of isolevoglucosenone
Richard H. Furneaux, Graeme J. Gainsford, Fred Shafizadeh et al. · Carbohydrate Research · 1986 · 36 citations