Stereoselective Radical Cyclization for the Synthesis of Bicyclic Higher-Carbon Sugars. Synthesis of the Sugar Moiety of Octosyl Acids.

Younosuke Araki,Tadatoshi Endo,Yoshifusa Arai,Masaki Tanji,Yoshiharu Ishido

ChemInform（1990）

Cited 33|Views0

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Abstract

The Bu3SnH - AIBN induced radical cyclization of 6-bromo-6-deoxy-3-O-[(E)-2-ethoxycarbonylethenyl]-1,2-O-isopropylidene-α-???-allofuranose (1) gave ethyl 3,7-anhydro-6,8-dideoxy-1,2-O-isopropylidene-α-???-glycero-???-allo-nonofuranuronate (2) in 80% yield. Similar cyclizations of furanose derivatives and a synthesis of the sugar moiety of octosyl acids were described.

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Key words

stereoselective radical cyclization,octosyl acids,synthesis,higher-carbon

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