Grignard-triggered fragmentation of vinylogous acyl triflates:: Synthesis of (Z)-6-heneicosen-11-one, the Douglas fir tussock moth sex pheromone

Grignard-triggered fragmentation of vinylogous acyl triflates:: Synthesis of (Z)-6-heneicosen-11-one, the Douglas fir tussock moth sex pheromone
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DOI:
10.1055/s-2006-939051
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发表时间:
2006-04-04
期刊:
影响因子:
2
通讯作者:
Dudley, GB
Dudley, GB
中科院分区:
化学4区
文献类型:
--
作者:
Jones, DM;Kamijo, S;Dudley, GB

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格氏试剂与乙烯基三氟酸酯在甲苯中通过加成-裂解反应生成炔基酮。用流线型合成(Z)-6-苯二酚-11- 1(道格拉斯冷杉丛蛾的性信息素)的实验证明了该方法的实用性。
Grignard reagents react with vinylogous acyl triflates in toluene via an addition-fragmentation sequence to afford alkynyl ketones. A streamlined synthesis of (Z)-6-heneicosen-11-one, the sex pheromone of the Douglas fir tussock moth, illustrates the utility of this method.