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- W2078145275 abstract "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 concise syntheses of the soft-coral constituents bissetone and palythazine in enantiopure form, thereby proving their absolute configuration. Moreover, several procedures are detailed to convert hydroxyglucal esters into 1,5-anhydro-d-fructose, their parent sugar, the direct low-temperature de-O-acylation being the most suitable for preparative purposes, as long as its access via enzymatic degradation of starch is not implemented on an appreciable scale." @default.
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- W2078145275 date "2008-02-01" @default.
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- W2078145275 title "Expedient conversion of d-glucose into 1,5-anhydro-d-fructose and into single stereogenic-center dihydropyranones, suitable six-carbon scaffolds for concise syntheses of the soft-coral constituents (−)-bissetone and (−)-palythazine" @default.
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- W2078145275 doi "https://doi.org/10.1016/j.tetasy.2008.01.019" @default.
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