Collective Total Synthesis of Ergot Alkaloids
Abstract
Ergot alkaloids represent a class of bioactive natural products that contain a tetrahydrobenzo[ cd ]indole structural unit. We report a structural unit-oriented collective total synthesis of nine tetracyclic ergot alkaloids. Among them, isopenniclavine and roquefortine A were synthesized for the first time. Key transformations of our strategy are a vinylogous arylation to establish the C10–C11 bond, an intramolecular diastereoselective vinylogous Mannich reaction to construct the critical tricyclic ergoline core along with two vicinal chiral stereocenters at C5 and C10, and a consecutive Mannich cyclization/reductive N -methylation to build the D ring.
Fields of Study & Subjects
Plant and fungal interactions
Advanced Synthetic Organic Chemistry
Chemical synthesis and alkaloids
Publication details
- Journal / source
- Organic Letters
- Publisher
- American Chemical Society (ACS)
- Volume
- 28
- Issue
- 14
- Pages
- 4524–4530
- Publication date
- 31 March 2026
- Language
- EN