Synthesis of (−)-8a-epi-Swainsonine, (1S,2R,8R,8aS)-Octahydro-1,2,8-indolizinetriol

(−)-8a-epi-Swainsonine (4), one of the stereocongeners of physiologically interesting indolizidine alkaloid (−)-swainsonine (1), has been synthesized starting from known methyl 3-azido-4,6-O-benzylidene-3-deoxy-α-D-altropyranoside. The α-D-mannosidase inhibitory activity of 4 was compared with natur...

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Bibliographic Details
Published inBulletin of the Chemical Society of Japan Vol. 60; no. 10; pp. 3667 - 3671
Main Authors Tadano, Kin-ichi, Hotta, Yukinori, Morita, Masahiro, Suami, Tetsuo, Winchester, Bryan, Bello, Isabello Centi di
Format Journal Article
LanguageEnglish
Published Tokyo The Chemical Society of Japan 01.10.1987
Chemical Society of Japan
Subjects
Chemistry
Exact sciences and technology
Heterocyclic compounds
Heterocyclic compounds with only one n hetero atom and condensed derivatives
Organic chemistry
Preparations and properties
Alkaloid
Angular nitrogen heterocycle
Epimer
Vinylic compound
Bicyclic compound
Enzyme inhibitor
Aldonic acid
Glycoside
Biological activity
α-D-Mannosidase
Enantiomer(-)
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Summary:(−)-8a-epi-Swainsonine (4), one of the stereocongeners of physiologically interesting indolizidine alkaloid (−)-swainsonine (1), has been synthesized starting from known methyl 3-azido-4,6-O-benzylidene-3-deoxy-α-D-altropyranoside. The α-D-mannosidase inhibitory activity of 4 was compared with natural 1.
ISSN:0009-2673
1348-0634
DOI:10.1246/bcsj.60.3667