A New Class of Glycosidase Inhibitor: Synthesis of Salacinol and Its Stereoisomers

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• 作者：Ahmad Ghavami ; Blair D. Johnston ; and B. Mario Pinto
• 刊名：Journal of Organic Chemistry
• 出版年：2001
• 出版时间：April 6, 2001
• 年：2001
• 卷：66
• 期：7
• 页码：2312 - 2317
• 全文大小：83K
• 年卷期：v.66,no.7(April 6, 2001)
• ISSN：1520-6904

文摘

Salacinol (4) is one of the active principles in the aqueous extracts of Salacia reticulata that aretraditionally 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 strategyrelies on the selective nucleophilic attack of 2,3,5-tri-O-benzyl-1,4-anhydro-4-thio-D- or L-arabinitolat C-1 of 2,4-O-benzylidene D- or L-erythritol-1,3-cyclic sulfate. The work serves to resolve theambiguity about the exact structure of salacinol and establishes conclusively the structure of thenatural product.