Synthesis of shikalkin and certain related compounds

  • V. L. Novikov
  • N. N. Balaneva
  • A. M. Moiseenkov
  • G. B. Elyakov
Organic Chemistry


A successful total synthesis of a biologically active pigment from plants of the Boraginaceae family was carried out with naphthazarine as the starting material, and using the 1,4,5,8-tetramethoxynaphthalene, the corresponding 2-vinyl derivative and its epoxide or a cyclopropane adduct with diazoacetic ester at the key stages. In the course of developing the scheme of the synthesis of shikalkin, its three analogs were obtained, differing in the nature of the monoterpenoid side chain.


shikonin alkannin shikalkin naphthazarine tetramethoxynaphthalene olefinization according to Wittig cyclopropyl-carbinylic rearrangement cerium-ammonium nitrate 


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Copyright information

© Plenum Publishing Corporation 1993

Authors and Affiliations

  • V. L. Novikov
  • N. N. Balaneva
  • A. M. Moiseenkov
  • G. B. Elyakov

There are no affiliations available

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