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Facile ring transformation from gluconolactone to cyclitol derivative via spiro sugar ortho ester
1School of Pharmaceutical Sciences, Teikyo University, Sagamiko, Kanagawa, Japan.
Organic Letters
|May 18, 2000
Abstract:
[reaction: see text] A short step preparation of cyclitol derivative 8 which is a versatile synthon for the synthesis of valiolamine and its related compounds is described. Key steps in this preparation are a novel enol ether formation from spiro sugar ortho esters with AlMe3 and an intramolecular Aldol condensation of alkyl enol ethers catalyzed by ZnCl2 in THF-H2O. With these reactions, gluconolactone derivative 1 was efficiently converted into 8 in short steps.