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Enantiospecific synthesis of polyhydroxylated indolizidines related to castanospermine:1 1-deoxy-castanospermine.

✍ Scribed by David Hendry; Leslie Hough; Anthony C. Richardson

Publisher
Elsevier Science
Year
1988
Tongue
French
Weight
597 KB
Volume
44
Category
Article
ISSN
0040-4020

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✦ Synopsis

Enantiospecific

synthesis of (6S,7R,8R,8aR)-6,7,8trihydroxyindolizidine (l-deoxy-castanospermine)

(3) is described from readily available D-glucose, where the key step involves oxidative bromination of a benzylidene acetal to afford 8-azido-3-0-benzoyl-5-bromo-5,6,7,8tetradeoxy-l,2-0-isopropylidene-~-L-ido-octose (16). The synthetic indolizidine (3) was tested against a range of glycosidases.

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