Total Synthesis of the Spirocyclic Bis‐Indole Alkaloid (−)‐Owerreine via a [4+2] Annulation
Abstract
We report the total synthesis of (-)-owerreine, a bis-indole alkaloid biosynthetically assembled from two deoxoapodine units. This aspidosperma monomeric template was synthesized via a domino Michael/Mannich/N-allylation sequence from a chiral indolyl-N-sulfinylimine and a DIAD-oxidation-promoted cycloetherification. It was further divergently transformed into an enamine precursor and an α,β-unsaturated indolenine, which were diastereoselectively assembled in the presence of the Eschenmoser salt through a [4+2] annulation. DFT calculations were deployed to gain insight into the mechanism and diastereoselectivity of this key step.
Fields of Study & Subjects
Alkaloids: synthesis and pharmacology
Synthesis and Characterization of Pyrroles
Marine Sponges and Natural Products
Publication details
- Journal / source
- Angewandte Chemie International Edition
- Publisher
- Wiley
- Volume
- 65
- Issue
- 17
- Pages
- e4281634–e4281634
- Publication date
- 12 March 2026
- Language
- EN