The chemistry of castanospermine. Direct oxidation of the tetraacetate to the corresponding γ-lactam

Graphic From the products of oxidation of tetra- O-acetylcastanospermine ( 2) with N-bromosuccinimide, only the γ-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...

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Bibliographic Details
Published in:Carbohydrate research 2004-07, Vol.339 (10), p.1747-1751
Main Authors: Furneaux, Richard H, Gainsford, Graeme J, Mason, Jennifer M, Tyler, Peter C
Format: Article
Language:English
Subjects:
Acetates - chemistry
Castanospermine
crystal structure
Crystallography, X-Ray
Enzyme Inhibitors - pharmacology
Indolizines - chemistry
Indolizines - isolation & purification
Lactam
lactams
Lactams - chemistry
Magnetic Resonance Spectroscopy
Methanol - chemistry
Methylene Chloride - chemistry
Models, Chemical
Models, Molecular
Oxidation
Oxidation-Reduction
Oxygen - chemistry
Plant Proteins - chemistry
Seeds - metabolism
Spectrophotometry
spermine
X-Rays
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Summary:Graphic From the products of oxidation of tetra- O-acetylcastanospermine ( 2) with N-bromosuccinimide, only the γ-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.
ISSN:0008-6215
1873-426X
DOI:10.1016/j.carres.2004.05.006