Challenging the Molecular Parameters of Vetiver: Can 4,5‐Dimethyl‐3‐(3′‐methylbut‐1′‐en‐2′‐yl)‐4‐phenylcyclopent‐2‐en‐1‐one Mimic Zizaenones in Structure and Odor? - Université Gustave Eiffel Accéder directement au contenu
Article Dans Une Revue European Journal of Organic Chemistry Année : 2019

Challenging the Molecular Parameters of Vetiver: Can 4,5‐Dimethyl‐3‐(3′‐methylbut‐1′‐en‐2′‐yl)‐4‐phenylcyclopent‐2‐en‐1‐one Mimic Zizaenones in Structure and Odor?

Philip Kraft

Résumé

In order to investigate the molecular parameters of vetiver odorants and scrutinize the significance of ziza‐6(13)‐en‐3‐ones as structural templates in the design of new vetiver odorants, 4,5‐dimethyl‐3‐(3′‐methylbut‐1′‐en‐2′‐yl)‐4‐phenylcyclopent‐2‐en‐1‐one ( 10 ) was synthesized in 6 steps from cyclopentane‐1,3‐dione ( 20 ) following a Stork–Danheiser strategy after synthetic approaches by Ni‐catalyzed [3+2] annulation and enyne metathesis had failed. Addition of EtOH, α‐methylation of the resulting vinylogous ester 18 , Pd‐catalyzed α‐arylation, and CeCl 3 · 2LiCl mediated alkylation with (3‐methylbut‐1‐en‐2‐yl)lithium, generated by Shapiro reaction from the corresponding hydrazone 23 , furnished after a concluding α‐methylation the target compound that possessed only a weak woody odor devoid of typical vetiver characteristics. While the design approach utilizing London dispersion forces could not reveal the secret of vetiver, it showed that the molecular parameters are far more complex than initially expected.
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Dates et versions

hal-04413167 , version 1 (23-01-2024)

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Citer

Patrick Pfaff, Halima Mouhib, Philip Kraft. Challenging the Molecular Parameters of Vetiver: Can 4,5‐Dimethyl‐3‐(3′‐methylbut‐1′‐en‐2′‐yl)‐4‐phenylcyclopent‐2‐en‐1‐one Mimic Zizaenones in Structure and Odor?. European Journal of Organic Chemistry, 2019, 2019 (15), pp.2643-2652. ⟨10.1002/ejoc.201900163⟩. ⟨hal-04413167⟩
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