Concise formal total synthesis of hybocarpone and related naturally occurring naphthazarins.

@article{Chai2006ConciseFT,
  title={Concise formal total synthesis of hybocarpone and related naturally occurring naphthazarins.},
  author={Christina Li Lin Chai and John A. Elix and Felicity K. E. Moore},
  journal={The Journal of organic chemistry},
  year={2006},
  volume={71 3},
  pages={
          992-1001
        }
}
A concise formal total synthesis of the cytotoxic bisnaphthazarin derivative hybocarpone has been completed through the development of routes to the synthetic precursor, 3-ethyl-2-hydroxy-5,7,8-trimethoxy-6-methyl-1,4-naphthoquinone. The oxidation of 3-ethyl-1,2,4,5,7,8-hexamethoxy-6-methylnaphthalene under Rapoport conditions gave 3-ethyl-2-hydroxy-5,7,8-trimethoxy-6-methyl-1,4-naphthoquinone in modest yields after basic hydrolysis. In addition, treatment of 3-ethyl-1,2,4,5,7,8-hexamethoxy-6… 
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19 Citations

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The formal total synthesis of hybocarpone was achieved in eight steps from commercially available 1,2,4-trimethoxybenzene using a modified CAN-mediated dimerization/hydration cascade sequence to generate the vicinal all-carbon quaternary centers in a stereocontrolled manner.

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Dysidavarone A, a structurally unprecedented sesquiterpenoid quinone, was synthesized in 30 % overall yield in a longest liner sequence of 13 steps from commercially available o-vanillin. A highly…

Recent Advances in the Chemistry and Biology of Natural Dimeric Quinones

Palladium-catalyzed annulation of alkynes with ortho-halide-containing benzyl alcohols in aqueous medium.

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