Work

Total Synthesis of the Spirocyclic Bis‐Indole Alkaloid (−)‐Owerreine via a [4+2] Annulation

Year: 2026

Type: article

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.

Source: Angewandte Chemie International Edition

DOI: 10.1002/anie.4281634

Authors: Elisa Coll, Vincent Gandon, Cyrille Kouklovsky, Laurent Evanno, Guillaume Vincent

Institutions: Centre National de la Recherche Scientifique, Université Paris-Saclay, Institut de Chimie Moléculaire et des Matériaux d'Orsay, Biomolécules : Conception, Isolement, Synthèse

Language: English

Topic: Advanced Synthetic Organic Chemistry

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: hybrid

Estimated APC paid: $5,510

Funders: Agence Nationale de la Recherche, Centre National de la Recherche Scientifique, Grand Équipement National De Calcul Intensif