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Stereocontrolled access to the octosyl acids - total synthesis of octosyl acid A

โœ Scribed by Hanessian, Stephen.; Kloss, John.; Sugawara, Tamio.

Book ID
125981235
Publisher
American Chemical Society
Year
1986
Tongue
English
Weight
284 KB
Volume
108
Category
Article
ISSN
0002-7863

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Stereoselective radical cyclization for
Stereoselective radical cyclization for the synthesis of bicyclic higher-carbon sugars. Synthesis of the sugar moiety of octosyl acids
โœ Younosuke Araki; Tadatoshi Endo; Yoshifusa Arai; Masaki Tanji; Yoshiharu Ishido ๐Ÿ“‚ Article ๐Ÿ“… 1989 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 282 KB

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.