Total Synthesis of Olivacine and Ellipticine via a Lactone Ring Opening and Aromatization Cascade


Dilek O., Patir S., TİLKİ T. , Erturk E.

JOURNAL OF ORGANIC CHEMISTRY, cilt.84, ss.7901-7916, 2019 (SCI İndekslerine Giren Dergi) identifier identifier identifier

  • Cilt numarası: 84 Konu: 12
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1021/acs.joc.9b00706
  • Dergi Adı: JOURNAL OF ORGANIC CHEMISTRY
  • Sayfa Sayıları: ss.7901-7916

Özet

Effective preparation of olivacine and ellipticine via late-stage D-ring cyclization is described. Key features of the synthetic routes include trifluoroacetic acid-mediated formation of a lactone that is fused to a tetrahydrocarbazole derivative and its one-pot two-step ring opening and aromatization mediated by para-toluenesulfonic acid and palladium on carbon, respectively.