Novel synthesis of castanospermine and 1-epicastanospermine.
[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.
Cronin
Linda
L
Department of Chemistry, Centre for Synthesis and Chemical Biology, Conway Institute of Biomolecular and Biomedical Research, University College Dublin, Belfield, Dublin 4, Ireland.
Murphy
Paul V
PV
D000586:Amination; D031291:Castanospermum / Q000737:chemistry; D002384:Catalysis; D007212:Indolizines / Q000138:chemical synthesis*; D015394:Molecular Structure; D010946:Plants, Medicinal / Q000737:chemistry; D013237:Stereoisomerism; D054836:Indolizidines
D007212:Indolizines; C037806:castanospermine; D054836:Indolizidines