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

@article{Shing2009CarbocyclizationOC,
  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},
  year={2009},
  volume={11 21},
  pages={
          5070-3
        }
}
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… 
22 Citations

Figures from this paper

Divergent Approach to Gabosines and Anhydrogabosines: Enantioselective Syntheses of (+)‐Epiepoformin, (+)‐EpoKformin, (+)‐Gabosine A, and Gabosines B and F
A divergent approach to polyoxygenated methylcyclohexanes has been applied to synthesize several gabosines and anhydrogabosines. The starting hydroxycyclohexenone, which is readily available in any
Stereoselective synthesis and relative configuration assignment of gabosine J.
TLDR
This work validates enone 1 as a general synthetic precursor for this kind of carbasugars as well as former syntheses of other gabosines and related compounds.
Carbocyclic Ring Closure of Aryl C-Glycosides Promoted by Fluoroboric Acid.
TLDR
A novel transformation from rhamnose-type C-glycosides to 2-cyclopentenones is described, which underwent ring-opening and subsequent Nazarov cyclization to afford 2-Wikipediaenones in good to excellent yields.
Total Synthesis and Glycosidase Inhibition Studies of (–)‐Gabosine J and Its Derivatives
TLDR
This is the first synthesis of a gabosine that employs mannitol as the starting material and the first report of the biological activity of gabOSine J.
...
1
2
3
...