Total Synthesis of Olivacine and Ellipticine via a Lactone Ring-Opening and Aromatization Cascade
Journal of Organic Chemistry, vol.84, no.12, pp.7901-7916, 2019 (SCI-Expanded, Scopus)
- 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.