Synthesis and chemistry of 2,3-dioxabicyclo[2.2.2]octane-5,6-diols.

@article{Valente2009SynthesisAC,
  title={Synthesis and chemistry of 2,3-dioxabicyclo[2.2.2]octane-5,6-diols.},
  author={Peter Valente and Thomas D. Avery and Dennis K. Taylor and Edward R. T. Tiekink},
  journal={The Journal of organic chemistry},
  year={2009},
  volume={74 1},
  pages={
          274-82
        }
}
1,4-Disubstituted 2,3-dioxabicyclo[2.2.2]oct-5-enes were dihydroxylated with osmium tetroxide to yield diols anti to the peroxide linkage in a highly selective manner. Reduction of the peroxide bond furnished cyclohexane-1,2,3,4-tetraols with toxocarol relative stereochemistry in excellent yield. This new methodology was employed to synthesize the natural product (1S,2R,3S,4R,5R)-2-methyl-5-(propan-2-yl)cyclohexane-1,2,3,4-tetrol (1) in a short sequence from (R)-alpha-phellandrene. Moreover… Expand
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