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, vol.84, no.12, pp.7901-7916, 2019 (SCI-Expanded, Scopus) identifier identifier

  • Publication Type: Article / Article
  • Volume: 84 Issue: 12
  • Publication Date: 2019
  • Doi Number: 10.1021/acs.joc.9b00706
  • Journal Name: Journal of Organic Chemistry
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7901-7916
  • Isparta University of Applied Sciences Affiliated: Yes

Abstract

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.