Fluorine in pheromones: Synthesis of fluorinated 12-dodecanolides as emerald ash borer pheromone mimetics
作者:Qingzhi Zhang、Charlotte S. Teschers、Ricardo Callejo、Mingyan Yang、Mingan Wang、Peter J. Silk、Krista Ryall、Lucas E. Roscoe、David B. Cordes、Alexandra M.Z. Slawin、David O'Hagan
DOI:10.1016/j.tet.2019.03.025
日期:2019.5
strategy to bias the conformational space accessed by these macrocycles, and to assess if the analogues may act as mimetics of 13-membered macrolide pheromones associated with the emerald ash borer. Accordingly individual syntheses of 5,5-difluoro- 5, 6,6-difluoro- 6, 7,7-difluoro- 7, 8,8-difluoro- 8 and 5,5,8,8-tetrafluoro- 9, 12-dodecanolides are outlined, and X-ray structural data were obtained for three
已经合成了一系列五个12个十二烷醇化物,它们在C5,C6,C7,C8处包含CF 2基团,在一种情况下,在C5和C8处进行双取代,以此作为偏置这些大环化合物进入的构象空间的策略,并且评估类似物是否可以充当与翡翠虫有关的13元大环内酯信息素的模拟物。的5,5-二氟-因此个别合成5,6,6-二氟- 6,7,7-二氟- 7,8,8-二氟- 8和5,5,8,8-四氟9,12- dodecanolides概述,和三(分别得到的X射线结构数据5,8和9)的这些化合物。结构清楚地表明,CF 2基团在大环中占据“角”位置,这与它们偏向可及构象的能力相符。含氟的十二-十二烷醇化物都在雌性甲虫中产生了电-血管造影反应。