71(P-57) ポリヒドロキシピペリジンアルカロイド類の全光学異性体合成(ポスター発表の部)

概要

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Polyhydroxylated nitrogen heterocycles azasugars may be considered to be mimics of sugars in which the ring oxygen has been substituted for a nitrogen atom. The often potent inhibitory activity of many of these compounds toward carbohydrate-processing enzymes has suggested their use in a wide range of potential therapeutic strategies including the treatment of viral infections, cancer, diabetes, tuberculosis, lysosomal storage diseases, and parasitic protozoa. Recently three fagomine 3-epi-fagomine, and 3,4-di-epi-fagomine were found from Xanthocercis zambesiaca occurring in southern Africa in dry forest and three 3,4,5-trihydroxypiperidines were also isolated from Eupatorium fortunei Turz. Some of them have been shown to have some activity against mammalian α-glucosidase and β-galactosidase. We describe herein a new entriy to the synthesis of all stereoisomers of fagomine including 4-epi-fagomine by the preparation of chiral building block: 2-silyloxymethyl 3-piperidene in a traightforward and stereoselective manner using the Garner aldehyde and catalytic ring-closing metathesis (RCM) for the construction of the piperidine ring. In addition, their inhibition of glycosidase activites were examined. Next, the stereoselective synthesis of all 3,4,5-trihydroxypiperidines using 4-piperiden-3-ol as building block obtained by the reaction of vinyl epoxide with allylamine followed by RCM is disclosed.
天然有機化合物討論会の論文
2003-09-01