Synthesis of 12-acetoxy-1, 3-dodecadiene, an insect sex pheromone of the red bollworm moth, from a butadiene telomer
作者:T. Mandai、H. Yasuda、M. Kaito、J. Tsuji、R. Yamaoka、H. Fukami
DOI:10.1016/0040-4020(79)80067-8
日期:1979.1
8-Phenoxy-1, 6-octadiene (1) formed by the Pd-catalyzed telomerization of butadiene with phonol was converted to 8-phenoxy-6-octen-1-ol (3). The alcohol 3 was converted to 8-iodo-1-phenoxy-2-octene (5). The Grignard reagent 7 prepared from 4-chloro 1-butyl tetrahydropranyl ether was coupled with the iodide 5 by the catalysis of CuI and bipyridyl to give 12-phenoxy-10-dodecen-1-ol (9), which was converted
通过丁二烯与苯酚的钯催化端粒化反应形成的8-苯氧基-1,6-辛二烯(1)被转化为8-苯氧基-6-辛烯-1-醇(3)。醇3被转化为8-碘-1-苯氧基-2-辛烯(5)。由4-氯1-丁基四氢戊基醚制得的格氏试剂7与碘化物5通过CuI和联吡啶基的催化作用偶合,得到12-苯氧基-10-十二碳烯-1-醇(9),将其转化为12-苯氧基乙酰氧基-1-苯氧基-2-十二碳烯(10)。最后,通过钯催化从苯氧基乙酰氧基-十二碳烯(10)中除去苯酚,获得了12-乙酰氧基-1,3-十二碳二烯(11)。