Journal
STUDIA UNIVERSITATIS BABES-BOLYAI CHEMIA
Volume 66, Issue 4, Pages 205-224Publisher
UNIV BABES-BOLYAI
DOI: 10.24193/subbchem.2021.4.15
Keywords
Cameraria ohridella; (8E; 10Z)-tetradeca-8; 10-dienal; Pheromone; Lure; Field Tests
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Funding
- Babes-Bolyai University, Raluca Ripan Institute for Research in Chemistry, Pheromone Production Center
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Versatile classical and modern methods were described for the new synthesis of (8E,10Z)-tetradeca-8,10-dienal using palladium, iron, or copper catalysts. The synthesis of the pure E,Z diastereoisomer revealed the diversity in the stereochemical aspects of pheromone communications.
Versatile classical and modern methods for a new synthesis of (8E,10Z)-tetradeca-8,10-dienal based on Sonogashira cross-coupling, Cahiez-Furstner reaction as well as other reactions using palladium, iron or copper as catalysts were described. We designed two ways employing two different strategies one of that involves an E-reduction and the other a Z- reduction with crucial importance in terms of diastereoselective synthesis. From the variously formulated pheromone baits, the one containing only the active isomer showed superior activity compared to the mixture of all isomers of 8,10-tetradecandienal. The synthesis of the pure E,Z diastereoisomer allowed to clarify their structure-bioactivity relationships to reveal the diversity in the stereochemical aspects of pheromone communications.
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