71(P-57) Synthesis of All Stereoisomers of Polyhydroxypiperidine Alkaloids

Takahata Hiroki, Mihara Yukiko, Ouchi Hidekazu, Banba Yasunori, Nemoto Hideo, Kato Atsushi, Adachi Isao

doi:10.24496/tennenyuki.45.0_419

Bibliographic Information

Other Title

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)

Abstract

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.

Journal

Symposium on the Chemistry of Natural Products, symposium papers

Symposium on the Chemistry of Natural Products, symposium papers 45 (0), 419-424, 2003

Symposium on the Chemistry of Natural Products Steering Committee

Details 詳細情報について

CRID: 1390001206079980544

NII Article ID: 110006682330

DOI: 10.24496/tennenyuki.45.0_419

ISSN: 24331856

Text Lang: ja

Data Source

JaLC
CiNii Articles

Abstract License Flag: Disallowed

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