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Stereoselective radical cyclization for the synthesis of bicyclic higher-carbon sugars. Synthesis of the sugar moiety of octosyl acids

✍ Scribed by Younosuke Araki; Tadatoshi Endo; Yoshifusa Arai; Masaki Tanji; Yoshiharu Ishido

Publisher
Elsevier Science
Year
1989
Tongue
French
Weight
282 KB
Volume
30
Category
Article
ISSN
0040-4039

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✦ Synopsis

The Bu3SnH -AIBN induced radical cyclization of 6-bromo-b-deoxy-3-~-[(~)-2-ethoxycarbonylethenyll_1,2-O_is-allofuranose (1) gave ethyl 3,7-anhydro-6,8-dideoxy-l,2-O-isopropylidene-~-~-glycero-~-allo-nono--furanuronate (2) in 80% yield.

Similar cvclizations of furanose derivatives and a synthesis.of the &gar moiety of oct&yl acids were described.

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