2-deoxyribose as a rich source of chiral 5-carbon building blocks.

@article{Wang20072deoxyriboseAA,
  title={2-deoxyribose as a rich source of chiral 5-carbon building blocks.},
  author={Dengjin Wang and William A Nugent},
  journal={The Journal of organic chemistry},
  year={2007},
  volume={72 19},
  pages={
          7307-12
        }
}
We have developed concise routes to a number of useful chiral 5-carbon synthetic building blocks using readily available O-1-methyl-2-deoxyribose as starting material. Novel transformations include the use of indium triflate to catalyze the oxidation of a methyl furanoside to the corresponding lactone with MCPBA and the Vasella-type fragmentation of a 5-iodo furanoside using chromium(II) chloride when zinc proved ineffective. In addition, 3,4-disubstituted piperidine derivatives were prepared… CONTINUE READING