ArticleAngewandte Chemie (International ed. in English)2026
Total Synthesis of the Spirocyclic Bis-Indole Alkaloid (-)-Owerreine via a [4+2] Annulation.
Article in Angewandte Chemie (International ed. in English), 2026. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 2 papers.
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2 citing papers in PubMed.
- Directed Heterodimerization: Total Synthesis of (-)-Folicangine, (-)-Voafolidine, (-)-Isovoafolidine, and (-)-Tabernaesine B.Organic letters · 2026Article
- Total Synthesis of the Spirocyclic Bis-Indole Alkaloid (-)-Owerreine via a [4+2] Annulation.Angewandte Chemie (International ed. in English) · 2026Article
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5 authors.
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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.
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