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

DİLEK Ö., Patir S., TİLKİ T., Ertürk E.

Journal of Organic Chemistry, cilt.84, sa.12, ss.7901-7916, 2019 (SCI-Expanded, Scopus) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 84 Sayı: 12
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1021/acs.joc.9b00706
  • Dergi Adı: Journal of Organic Chemistry
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.7901-7916
  • Isparta Uygulamalı Bilimler Üniversitesi Adresli: Evet

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.