Studies of the synthesis of providencin: construction and assembly of two major subunits.

@article{White2014StudiesOT,
  title={Studies of the synthesis of providencin: construction and assembly of two major subunits.},
  author={James D White and S. Jana},
  journal={The Journal of organic chemistry},
  year={2014},
  volume={79 2},
  pages={
          700-10
        }
}
The "northern" sector of the cembranoid diterpene providencin containing a tetrasubstituted cyclobutane was synthesized from the bis(acetonide) of d-glucose using dicyclopentadienylzirconium(0)-mediated oxygen abstraction from a furanose. Oxidative scission of the vinyl substituent of this cyclobutane gave an aldehyde, which was reacted with an alkynylstannane to provide an allenol. Cyclization of the derived allenone with silver nitrate led to a cyclobutylfuran comprising the northern subunit… Expand
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