CARB 6 |
| Because we discovered by quantum calculations that a carbonyl group homoconjugated with an electro-deficient moiety can be electron-releasing (frangomeric effect of the non-bonding electron pairs of the carbonyl group), synthetic intermediates were searched that would exploit this property. This has led to the development of enantiomerically pure 7-oxabicyclo[2.2.1]hept-5-en-2-yl derivatives (the “Naked Sugars” ) as new “chirons”. These compounds are useful starting materials in the synthesis of rare carbohydrates and analogues, including azasugars, carbasugars, C-nucleosides, C-glycosides, conduritols, conduramines, indolizidines, C-disaccharides, aza-C-disaccharides, etc. More recently the “Aza-Naked-Sugars” (7-azabicyclo[2.2.1]hept-5-en-2-yl derivatives) have been developed and found to be useful scaffolds for medicinal chemistry. Some of the unusual carbohydrates analogues so-obtained show interesting biological activities that will be reviewed. |
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Claude S. Hudson Award in Carbohydrate Chemistry: Symposium in Honor of Pierre Sina˙
8:45 AM-12:10 PM, Sunday, March 25, 2007 McCormick Place North -- Room N226, Level 2, Oral
Division of Carbohydrate Chemistry |