Expedient conversion of d-glucose into 1, 5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise …
High-yielding protocols are described to convert d-glucose—via hydroxylaminolysis of its hydroxyglucal esters, followed by deoximination and β-elimination of acid—into dihydropyranone building blocks with a single stereogenic center. Their versatility as enantiopure six-carbon scaffolds is highlighted by excellent regio-and stereocontrol in a variety of addition reactions and by their straightforward use as building blocks for the ...
