A succinct access to ω-hydroxylated jasmonates via olefin metathesis

被引:2
|
作者
Jimenez-Aleman, Guillermo H. [1 ]
Secinti, Selina [1 ]
Boland, Wilhelm [1 ]
机构
[1] Max Planck Inst Chem Ecol, Dept Bioorgan Chem, D-07745 Jena, Germany
来源
ZEITSCHRIFT FUR NATURFORSCHUNG SECTION C-A JOURNAL OF BIOSCIENCES | 2017年 / 72卷 / 7-8期
关键词
cross-metathesis; gram scale synthesis; jasmonate; phytohormone; omega-hydroxylated jasmonate; SELECTIVE CROSS-METATHESIS; JA-ILE-MACROLACTONES; RUTHENIUM CATALYSTS; ACID; ARABIDOPSIS; ISOLEUCINE; (+)-7-ISO-JASMONOYL-L-ISOLEUCINE; CYTOCHROME-P450; BIOSYNTHESIS; KETOLACTONE;
D O I
10.1515/znc-2017-0104
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
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, omega-oxidized compounds form an important subfamily. The biological roles of these omega-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 omega-oxidized jasmonates is described. The approach utilizes olefin cross-metathesis as the key step employing inexpensive, commercially available substrates and catalysts.
引用
收藏
页码:285 / 292
页数:8
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