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Efficient syntheses of (10E,12Z,15Z)-9-oxo- and (9Z,11E,15E)-13-oxo-octadecatrienoic acids; two stress metabolites of wounded plants
Tetrahedron ( IF 2.1 ) Pub Date : 15 April 2002 , DOI: 10.1016/s0040-4020(02)00231-4
Thomas Koch , Michal Hoskovec , Wilhelm Boland

Configurationally pure 9-oxo-10E,12Z,15Z- and 13-oxo-9Z,11E,15E-octadecatrienoic acid are available from linolenic acid via regioselective functionalisation using lipoxygenases from soybean or tomato at specific pH conditions. Reduction of the resulting hydroperoxides followed by oxidation of the resulting allylic alcohols with Bobbitt's reagent yields the configurationally pure but labile ketotrienoic acids 4 and 5 without concomitant isomerisation.

中文翻译:

(10 E,12 Z,15 Z)-9-氧代-和(9 Z,11 E,15 E)-13-氧代-十八碳三烯酸的高效合成; 受伤植物的两种胁迫代谢产物

可以在特定pH条件下,使用大豆或番茄的脂加氧酶通过区域选择性官能化从亚麻酸中获得结构纯的9-oxo-10 E,12 Z,15 Z-和13-oxo-9 Z,11 E,15 E-十八碳三烯酸。还原得到的氢过氧化物,然后用Bobbitt试剂氧化得到的烯丙醇,得到结构纯净但不稳定的酮三烯酸45,而没有伴随的异构化。
更新日期:2017-01-31
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