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ChemInform Abstract: Synthesis of (1R,2R,3R,7R,7aR)-Hexahydro-3- (hydroxymethyl)-1H-pyrrolizine-1,2,7-triol: 7-Epiaustraline.

✍ Scribed by S. E. DENMARK; B. HERBERT

Publisher: John Wiley and Sons
Year: 2010
Weight: 34 KB
Volume: 29
Category: Article
ISSN: 0931-7597
DOI: 10.1002/chin.199848247

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✦ Synopsis

Synthesis of (1R,2R,3R,7R,7aR)-Hexahydro-3-(hydroxymethyl)-1Hpyrrolizine-1,2,7-triol: 7-Epiaustraline.

-Title compound (VI) is synthesized from known nitronate (I), prepared via [4 + 2] cycloaddition, in order to establish [4 + 2]/[3 + 2] cycloaddition chemistry as a general strategy for the synthesis of alexines and australines, pyrrolizidine alkaloids possessing glucosidase inhibitory and antiviral activities, for example. -(DENMARK,

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