A New Class of Glycosidase Inhibitor: Synthesis of Salacinol and Its Stereoisomers
- 10 March 2001
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 66 (7) , 2312-2317
- https://doi.org/10.1021/jo001444g
Abstract
Salacinol (4) is one of the active principles in the aqueous extracts of Salacia reticulata that are traditionally used in Sri Lanka and India for the treatment of diabetes. The syntheses of salacinol (4), the enantiomer of salacinol (5), and a diastereomer (7) are described. The synthetic strategy relies on the selective nucleophilic attack of 2,3,5-tri-O-benzyl-1,4-anhydro-4-thio-d- or l-arabinitol at C-1 of 2,4-O-benzylidene d- or l-erythritol-1,3-cyclic sulfate. The work serves to resolve the ambiguity about the exact structure of salacinol and establishes conclusively the structure of the natural product.Keywords
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