New synthetic pathways to the Anastrepha ludens host marking pheromone: harnessing iridium-catalysis with novel P,N-ligand for enantioselective construction

A highly efficient iridium-catalyzed asymmetric hydrogenation approach is described for the total synthesis of the biologically active (R,L) A. ludens host marking pheromone (HMP). By utilizing a novel Ir(i)-complex and a chiral P,N-ligand, excellent enantioselectivities of up to 94% ee were achieve...

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Bibliographic Details
Published in:Organic chemistry frontiers an international journal of organic chemistry 2023-08, Vol.10 (19), p.4827-4835
Main Authors: Tushar Janardan Pawar, Barcelona-Cazanave, Liliette, Bonilla-Landa, Israel, Escobar, Magdalena, Jimenez-Halla, J Oscar C, Altúzar-Molina, Alma, Romero-Arellano, Patricia, Edmunds, Andrew J F, Aluja, Martín, Olivares-Romero, José Luis
Format: Article
Language:English
Subjects:
Asymmetry
Biological activity
Catalysis
Chemical synthesis
Computer applications
Enantiomers
Iridium
Ligands
Marking
Marking pheromone
Organic chemistry
Pest control
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Summary:A highly efficient iridium-catalyzed asymmetric hydrogenation approach is described for the total synthesis of the biologically active (R,L) A. ludens host marking pheromone (HMP). By utilizing a novel Ir(i)-complex and a chiral P,N-ligand, excellent enantioselectivities of up to 94% ee were achieved. The streamlined synthetic route involves seven reaction steps, offering improved efficiency and shorter synthesis timelines compared to previous methods. The mechanism of this reaction was studied using computational methods, providing valuable insights into the catalytic process. The synthesized (R,L)-14A. ludens HMP was evaluated in biological assays, demonstrating its efficacy to reduce the number of ovipositions and egg clutches laid by females of the pestiferous tephritid fly A. ludens. These findings have significant implications for pest control strategies and advancements in compound synthesis. This work represents a noteworthy contribution to the field of asymmetric catalysis and chemical biology, combining experimental and computational approaches to achieve efficient synthesis and gain mechanistic understanding.
ISSN:2052-4110
2052-4110
DOI:10.1039/d3qo01093g