Eco-Friendly and Industrially Scalable Synthesis of the Sex Pheromone of <i>Lobesia botrana</i>. Important Progress for the Eco-Protection of Vineyard

Cahiez, Gérard; Guerret, Olivier; Moyeux, Alban; Dufour, Samuel; Lefèvre, Nicolas

doi:10.1021/acs.oprd.7b00206

Cited by 20 publications

(84 citation statements)

References 25 publications

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“…More recently,C ahiez and co-workers at Chimie Paris-Te ch in collaboration with M2i reported the iron-catalyzed cross-coupling of av inyl phosphate with an in situ generated alkyl magnesium chloride in the synthesis of the sex pheromone of Lobesia botrana as apotential crop protection agent (Scheme 8). [49] Contrary to studies with aryl electrophiles,the use of the dienyl phosphate [50] allowed for ahighly efficient cross-coupling at low catalyst loading (0.05-0.10 mol %). This example forecasts an exciting possibility of iron-catalyzed cross-couplings with high turnover numbers as an ecologically friendly approach to sustainable base-metal catalysis.…”

Section: Methodsmentioning

confidence: 99%

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

2018

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The scarcity of precious metals has led to the development of sustainable strategies for metal-catalyzed cross-coupling reactions. The establishment of new catalytic methods using iron is attractive owing to the low cost, abundance, ready availability, and very low toxicity of iron. In the last few years, sustainable methods for iron-catalyzed cross-couplings have entered the critical area of pharmaceutical research. Most notably, iron is one of the very few metals that have been successfully field-tested as highly effective base-metal catalysts in practical, kilogram-scale industrial cross-couplings. In this Minireview, we critically discuss the strategic benefits of using iron catalysts as green and sustainable alternatives to precious metals in cross-coupling applications for the synthesis of pharmaceuticals. The Minireview provides an essential introduction to the fundamental aspects of practical iron catalysis, highlights areas for improvement, and identifies new fields to be explored.

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Section: Methodsmentioning

confidence: 99%

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

2018

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“…This has been inspired by our previous work on synthesis of the sex pheromone of Lobesia botrana: we could indeed demonstrate that α,ω-magnesium alkoxide salts of Grignard reagents could be used as efficient nucleophiles in ligand-and additive-free iron-catalyzed cross-couplings with alkenyl electrophiles. 5 Applying this strategy to the convergent synthesis of 1, the Grignard reagent of 7-magnesium alkoxide salt 5 is subjected to an iron-catalyzed Kumada cross-coupling with diastereomerically pure (1E,3Z)-dienol phosphate 6a. Preparation of synthons 5 and 6a as well as the cross-coupling step are detailed thereafter.…”

Section: Resultsmentioning

confidence: 99%

“…Preparation of the C1─C7 synthon (5). Diethyl pimelate 2 was chosen as a starting material for the construction of the C1─C7 chain (Scheme 2).…”

Section: Resultsmentioning

confidence: 99%

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Short and Easily Scalable Synthesis of the Sex Pheromone of the Horse-Chestnut Leaf Miner (Cameraria ohridella) Relying on a Key Ligand- and Additive-Free Iron-Catalyzed Cross-Coupling

Chourreu

Guerret²,

Guillonneau³

et al. 2020

Org. Process Res. Dev.

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We describe in this work a short 6-step convergent high-scale synthesis of the sex pheromone of the horse-chestnut leaf miner (8E,10Z-tetradeca-8,10-dienal). This procedure relies on a key stereoselective iron-catalyzed Kumada cross-coupling, which affords the coupling product with a high yield in the absence of additional ligands or additives. DFT calculations moreover suggest that ω-alkoxide groups on iron-ligated chains in transient organoiron(II) intermediates can enhance their stability and hamper their decomposition in off-cycle β-hydride elimination reactions.

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“…A high purity standard of (E,Z)-7,9-dodecadien-1-yl acetate (ca. 95%) was obtained after purification of the supplied sample by gravity column (silica gel containing 10% of AgNO 3 ; eluent: 3% Et 2 O/hexane), which had spectroscopic properties identical to those described in the literature [37].…”

Section: Chemicals and Reagentsmentioning

confidence: 97%

Airborne Pheromone Quantification in Treated Vineyards with Different Mating Disruption Dispensers against Lobesia botrana

Gavara

Vacas

Navarro³

et al. 2020

Insects

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Mating disruption (MD) is widely used against the European grapevine moth (EGVM), Lobesia botrana (Denis and Schiffermüller; Lepidoptera: Tortricidae), by installing passive dispensers or aerosol devices. The present work reports a new sampling and quantification methodology to obtain absolute data about field airborne pheromone concentration based on air samplings and sensitive chromatographic-spectroscopic methods. Samplings were performed in fields treated with passive dispensers or aerosol devices at different moments throughout the crop cycle to study how they act and how the disruption is triggered. Moreover, pheromone adsorption and releasing capacity of vine leaves were studied to elucidate their role in the disruption. Although both types of dispensers were effective in limiting the damage inflicted by EGVM, they performed differently and provided different airborne pheromone concentration profiles. Results also proved that leaves were able to adsorb and release part of the airborne pheromone acting as subsequent and additional pheromone sources. This fact could explain the different concentration profiles. Moreover, our results suggest that lower pheromone emission than that of the current passive dispensers still could provide an adequate performance in the field. Competitive mechanisms involved in MD using both dispensers, the dynamics of the airborne pheromone throughout the time and the importance of the canopy are discussed.

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Eco-Friendly and Industrially Scalable Synthesis of the Sex Pheromone of Lobesia botrana. Important Progress for the Eco-Protection of Vineyard

Abstract: A one-pot synthesis of the pheromone of Lobesia botrana is described. The procedure allows an efficient and economical access to this product which is used for the protection of vineyards.

Cited by 20 publications

References 25 publications

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

Iron‐Catalyzed Cross‐Couplings in the Synthesis of Pharmaceuticals: In Pursuit of Sustainability

Short and Easily Scalable Synthesis of the Sex Pheromone of the Horse-Chestnut Leaf Miner (Cameraria ohridella) Relying on a Key Ligand- and Additive-Free Iron-Catalyzed Cross-Coupling

Airborne Pheromone Quantification in Treated Vineyards with Different Mating Disruption Dispensers against Lobesia botrana

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