Carbocyclization of carbohydrates: diastereoselective synthesis of (+)-gabosine F, (-)-gabosine O, and (+)-4-epi-gabosine O.

  title={Carbocyclization of carbohydrates: diastereoselective synthesis of (+)-gabosine F, (-)-gabosine O, and (+)-4-epi-gabosine O.},
  author={Tony Kung Ming Shing and King Ho So and Wun S. Kwok},
  journal={Organic letters},
  volume={11 21},
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 in 12 steps with 23% overall yield, thereby confirming its absolute configuration. Similarly, efficient syntheses of gabosine O and 4-epi-gabosine O were accomplished from D-mannose in 9 and 11 steps with 41% and 38% overall yields, respectively, involving INOC, regioselective dehydration… 
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