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- W2050903553 abstract "The total synthesis of ()-xyloketal D and its enantiomer have been achieved by the reaction of an ortho-quinone methide with (4R)- and (4S)-4,5-dihydro-2,4-dimethylfuran via a diastereoselective inverse electron demand DielsAlder reaction. This total synthesis confirmed the absolute stereochemistry of the natural product. The ortho-quinone methide was generated by reaction of an appropriately functionalized Mannich base with methyl iodide. The Mannich base was prepared in one step from 2,4-dihydroxyacetophenone, formaldehyde, and morpholine. The enantiomeric dihydrofurans were prepared from (2R)- and (2S)-2-methylpent-4-ynoic acid via a three-step reaction sequence. These chiral nonracemic synthetic precursors were prepared from the corresponding (R)-phenylglycinol-derived diastereomeric amides of the readily available racemic carboxylic acid. The absolute stereochemistry of these carboxylic acids was firmly established by conversion to a known compound that had been previously prepared from a chiral pool starting material.Key words: xyloketal D, inverse electron demand DielsAlder reaction, ortho-quinone methide, dihydrofuran." @default.
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- W2050903553 date "2004-11-01" @default.
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- W2050903553 title "Total synthesis of ()-xyloketal D and its enantiomer Confirmation of absolute stereochemistry" @default.
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- W2050903553 doi "https://doi.org/10.1139/v04-138" @default.
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