The chemistry of castanospermine. Direct oxidation of the tetraacetate to the corresponding gamma-lactam.
From the products of oxidation of tetra-O-acetylcastanospermine (2) with N-bromosuccinimide, only the gamma-lactam 11 was isolated (19%). Treatment of this lactam with DBU in dichloromethane afforded the elimination product 12, while deacetylation with sodium methoxide in methanol gave tetraol 13 together with diene 14. The X-ray crystal structure of compound 13 is reported.
Furneaux
Richard H
RH
Industrial Research Ltd, PO Box 31-310, Lower Hutt, New Zealand.
Gainsford
Graeme J
GJ
Mason
Jennifer M
JM
Tyler
Peter C
PC
D000085:Acetates / Q000737:chemistry*; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000494:pharmacology; D007212:Indolizines / Q000737:chemistry* / Q000302:isolation & purification; D007769:Lactams / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D000432:Methanol / Q000737:chemistry; D008752:Methylene Chloride / Q000737:chemistry; D008956:Models, Chemical; D008958:Models, Molecular; D010084:Oxidation-Reduction; D010100:Oxygen / Q000737:chemistry*; D010940:Plant Proteins / Q000737:chemistry; D012639:Seeds / Q000378:metabolism; D013053:Spectrophotometry; D014965:X-Rays; D054836:Indolizidines
D000085:Acetates; D004791:Enzyme Inhibitors; D007212:Indolizines; D007769:Lactams; D000432:Methanol; D008752:Methylene Chloride; D010100:Oxygen; D010940:Plant Proteins; C037806:castanospermine; D054836:Indolizidines