Novel synthesis of castanospermine and 1-epicastanospermine.

Abstract

[reaction: see text] Polyhydroxylated indolizidines have potential for treatment of HIV, hepatitis C and HSV infection, multiple sclerosis, angiogenesis, cancer, and diabetes. A new synthetic approach to the title compounds from a 5-C-methoxypyranosyl azide has been developed. The route incorporates the aldol reaction and a novel catalytic reductive amination cascade to generate the indolizidine ring.

• Authors: Linda Cronin, Paul V Murphy
• Journal: Organic letters (Org Lett) Vol. 7 Issue 13 Pg. 2691-3 (Jun 23 2005) ISSN: 1523-7060 [Print] United States
• PMID: 15957923 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Indolizines
• castanospermine

Topics

• Amination
• Castanospermum (chemistry)
• Catalysis
• Indolizines (chemical synthesis)
• Molecular Structure
• Plants, Medicinal (chemistry)
• Stereoisomerism