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Intramolecular nitrile oxide-alkene cycloaddition of sugar derivatives with unmasked hydroxyl group(s).
The INOC reaction, using chloramine-T, in the presence of silica gel, to generate nitrile oxides from oximes, proceeded smoothly to afford five- or six-membered carbocycles in good to excellent yields.
Carbocyclization of carbohydrates: diastereoselective synthesis of (+)-gabosine F, (-)-gabosine O, and (+)-4-epi-gabosine O.
Exploitation of silica gel/chloramine T mediated intramolecular nitrile oxide-alkene cycloaddition (INOC) of sugar-derived oximes to carbocycles furnished the first synthesis of gabosine F from l-arabinose, thereby confirming its absolute configuration.
CCDC 621694: Experimental Crystal Structure Determination
Related Article: Tony K.M.Shing, Wai F.Wong, Hau M.Cheng, Wun S.Kwok, King H.So|2007|Org.Lett.|9|753|doi:10.1021/ol062873p