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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Aromatization Reactions of Castanospermine Tetraacetate

RFC Brown, DJ Collins, LM Lagniton, RJ Smith and NR Wong

Australian Journal of Chemistry 45(2) 469 - 474
Published: 1992

Abstract

The Polonovski reaction of castanospermine tetraacetate N-oxide with acetic anhydride gave (±)-1-acetoxy-8-hydroxy-2,3-dihydro-lH-indolizinium acetate (10) by aromatization of the piperidine ring. N- Bromosuccinimide oxidation of castanospermine tetraacetate gave a low yield (4%) of (+)-2-bromo-5,6,7,8-tetrahydroindolizine-6,7,8-triyl triacetate (13), by aromatization of the pyrrolidine ring.

https://doi.org/10.1071/CH9920469

© CSIRO 1992

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