An approach to the synthesis of the Prelog–Djerassi lactone using D-glucose as a starting material is described. The use of Swern oxidation provides an efficient means of preparing carbohydrate ketones. An unusual departure from the normal reaction pathway of the Peterson reaction has been observed, and has been found to depend on the stereochemistry of the intermediate β-hydroxysilanes.
K. Jones and W. W. Wood, J. Chem. Soc., Perkin Trans. 1, 1987, 537 DOI: 10.1039/P19870000537
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