New Synthesis of Pine Sawfly Pheromones

被引:0
|
作者
He, Guo-Guo [1 ]
Yang, Xuan [2 ]
Cheng, Yu [2 ]
Bai, Hong-Jin [1 ]
Zhang, Tao [2 ]
Du, Zhen-Ting [2 ,3 ]
机构
[1] Tarim Univ, Engn Lab Chem Resources Utilizat South Xinjiang, Xinjiang Prod & Construct Corps, Alar 843300, Peoples R China
[2] Northwest A&F Univ, Coll Chem & Pharm, Yangling 712100, Shaanxi, Peoples R China
[3] Key Lab Bot Pesticide R&D Shaanxi Prov, Yangling 712100, Shaanxi, Peoples R China
关键词
pine sawfly pheromones; stereocenters; (2S; 3S; 7S)-3; 7-dimethylpentadecan-2-ol; SEX-PHEROMONE; 3,7-DIMETHYLPENTADEC-2-YL ACETATE; ASYMMETRIC-SYNTHESIS; NEODIPRION-SERTIFER; ATTRACTANTS; COMPONENTS;
D O I
10.1134/S1070428022090172
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Based on the previously synthesized chiral intermediate, a new synthesis of pine sawfly pheromones bearing 3 stereocenters has been achieved. The key steps were Evans' template induction, Wittig olefina-tion, and conventional chemical operations. (2S,3S,7S)-3,7-Dimethylpentadecan-2-yl acetate and propanoate were obtained in 9 steps with an overall yield of 34%.
引用
收藏
页码:1311 / 1318
页数:8
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