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A succinct access to omega-hydroxylated jasmonates via olefin metathesis

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Jimenez-Aleman,  Guillermo Hugo
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;
IMPRS on Ecological Interactions, MPI for Chemical Ecology, Max Planck Society;

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Secinti,  Selina
Department of Biochemistry, Prof. J. Gershenzon, MPI for Chemical Ecology, Max Planck Society;

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Boland,  Wilhelm
Department of Bioorganic Chemistry, Prof. Dr. W. Boland, MPI for Chemical Ecology, Max Planck Society;

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Citation

Jimenez-Aleman, G. H., Secinti, S., & Boland, W. (2017). A succinct access to omega-hydroxylated jasmonates via olefin metathesis. Zeitschrift für Naturforschung, C: Journal of Biosciences, 72(7-8), 285-292. doi:10.1515/znc-2017-0104.


Cite as: https://hdl.handle.net/11858/00-001M-0000-002D-6F0C-8
Abstract
In higher plants, jasmonates are lipid-derived signaling molecules that control many physiological processes, including responses to abiotic stress, defenses against insects and pathogens, and development. Among jasmonates, ω-oxidized compounds form an important subfamily. The biological roles of these ω-modified derivatives are not fully understood, largely due to their limited availability. Herein, a brief (two-step), simple and efficient (>80% yield), versatile, gram-scalable, and environmentally friendly synthetic route to ω-oxidized jasmonates is described. The approach utilizes olefin cross-metathesis as the key step employing inexpensive, commercially available substrates and catalysts.