SYNTHESIS OF SHIKALKIN AND CERTAIN RALATED COMPOUNDS

Article abstract of DOI:10.1007/BF00864352

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