Sequential Alkene Isomerization and Ring-Closing Metathesis in Production of Macrocyclic Musks from Biomass

被引：24
作者：
Sytniczuk, Adrian [1 ]
Forcher, Gwenael [1 ]
Grotjahn, Douglas B. [2 ]
Grela, Karol [1 ,3 ]
机构：
[1] Univ Warsaw, Fac Chem, Biol & Chem Res Ctr, Zwirki & Wigury 101, PL-02089 Warsaw, Poland
[2] San Diego State Univ, Dept Chem & Biochem, 5500 Campanile Dr, San Diego, CA 92182 USA
[3] Polish Acad Sci, Inst Organ Chem, Kasprzaka 44-52,POB 58, PL-01224 Warsaw, Poland
来源：
CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 41期
关键词：
biomass; isomerization; macrocyclization; metathesis; musk; TRANSITION-METAL-COMPLEXES; DOUBLE-BOND MIGRATION; OLEFIN METATHESIS; BIFUNCTIONAL CATALYST; RUTHENIUM COMPLEXES; HIGHLY EFFICIENT; METALLACYCLOBUTANE DEPROTONATION; DECOMPOSITION; ETHENOLYSIS; STRATEGY;
D O I：
10.1002/chem.201800728
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
We report successful utilization of sequential alkene isomerization and ring-closing metathesis of dec-9-enoic acid based dienes in synthesis of macrocyclic lactones that possess a strong scent of musk. This catalytic sequence was essential to trim the chain length of starting dienes to yield macrocycles of the right size. Dec-9-enoic acid is conveniently obtainable from oleic esters by Ru-catalysed ethenolysis.
引用
收藏
页码：10403 / 10408
页数：6
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