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Updated: Sep 27, 2025

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Asymmetric Divergent Total Syntheses of (+)-Decursivine and (+)- Serotobenine via Intramolecular Fischer Indole
Dong-Hyun Kim1, Hyo-Mi Kim1, Ji-Su Lim1
1Center for New Directions in Organic Synthesis, Department of Chemistry, Hanyang University, 222 Wangsimni-ro, Seongdong-gu, Seoul 04763, Korea.
Abstract:
A new asymmetric synthetic route to (+)-decursivine and (+)-serotobenine is formulated. The key developments are the de novo construction of the crucial eight-membered 3,4-fused tricyclic indole ring engaged by the intramolecular Fischer indole synthesis and the stereocontrolled assembly of the dihydrobenzofuran subunit mediated by the asymmetric intramolecular Rh-carbenoid C-H insertion. BF3-mediated selective C15 epimerization followed by removal of the amine masking groups completed the target natural compounds' asymmetric and divergent total syntheses.
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