Enantioselective Total Synthesis of (−)-Vallesamidine Enabled by Asymmetric Hydrogenation and Aza-Wacker Cyclization to Construct the Core Spirocyclopentane-1,2′-indoline Structure DOI
F. Yang,

Xia-Lin Wang,

Fengqian Zhao

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 22, 2025

An enantioselective total synthesis of (-)-vallesamidine is described, integrating asymmetric hydrogenation with aza-Wacker cyclization to form the chiral spirocyclopentane-1,2'-indoline. Intramolecular Stetter reaction and alkylation are employed construct a tetracyclic framework featuring quaternary carbon center. Schmidt rearrangement intramolecular aldol condensation facilitate formation D E rings. This achieves in 14 steps an overall yield 4.2% from exocyclic enone ester.

Language: Английский

Enantioselective Total Synthesis of (−)-Vallesamidine Enabled by Asymmetric Hydrogenation and Aza-Wacker Cyclization to Construct the Core Spirocyclopentane-1,2′-indoline Structure DOI
F. Yang,

Xia-Lin Wang,

Fengqian Zhao

et al.

Organic Letters, Journal Year: 2025, Volume and Issue: unknown

Published: May 22, 2025

An enantioselective total synthesis of (-)-vallesamidine is described, integrating asymmetric hydrogenation with aza-Wacker cyclization to form the chiral spirocyclopentane-1,2'-indoline. Intramolecular Stetter reaction and alkylation are employed construct a tetracyclic framework featuring quaternary carbon center. Schmidt rearrangement intramolecular aldol condensation facilitate formation D E rings. This achieves in 14 steps an overall yield 4.2% from exocyclic enone ester.

Language: Английский

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