Asymmetric Synthesis of Contact Pheromone Component of Xylotrechus colonus and Its Analogues

被引：0

作者：

Yuan, Chaonan ^{[1
]}

Wu, Jianwei ^{[1
]}

Yu, Shihang ^{[1
]}

Bian, Qinghua ^{[1
]}

Wang, Min ^{[1
]}

Liu, Dan ^{[1
]}

Zhong, Jiangchun ^{[1
]}

机构：

[1] China Agr Univ, Dept Appl Chem, 2 West Yuanmingyuan Rd, Beijing 100193, Peoples R China

来源：

CHEMISTRYSELECT | 2023年 / 8卷 / 13期

关键词：

asymmetric synthesis; catalytic hydrogenation; chiral phosphonium salt; contact pheromone; Xylotrechus colonus; SEX-PHEROMONE; METATHESIS; RING;

D O I：

10.1002/slct.202204807

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Xylotrechus colonus is an abundant wood-boring pest of woody plants. 3-Methylpentacosane was identified as the component of its contact pheromone. A novel and efficient asymmetric synthesis of (S)-3-methylpentacosane and its analogues was developed using (S)-2-methylbutan-1-ol as chiral source. The key of this approach included Wittig coupling of chiral phosphonium salt with aldehyde, Pd-catalyzed hydrogenation and Appel reaction. Our synthesis would be helpful for the control and detect of this pest.

引用

页数：5

共 50 条

[41] Asymmetric synthesis of (S)-2-sec-Butyl-4,5-dihydrothiazole, a pheromone component of the Mus musculus
Lu, C. F.
Hu, F. Q.
Yang, G. C.
Chen, Z. X.
CHEMISTRY OF NATURAL COMPOUNDS, 2012, 48 (05) : 860 - 862
[42] Synthesis and Electrophysiological Testing of Carbonyl Pheromone Analogues for Carposinid Moths
Twidle, Andrew M.
Pilkington, Lisa, I
Suckling, David M.
Barker, David
ACS OMEGA, 2021, 6 (32): : 21016 - 21023
[43] Asymmetric Total Synthesis of (+)-Phainanoid A and Biological Evaluation of the Natural Product and Its Synthetic Analogues
Xie, Jiaxin
Zheng, Zhong
Liu, Xin
Zhang, Nan
Choi, Shinyoung
He, Chuan
Dong, Guangbin
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2023, 145 (08) : 4828 - 4852
[44] Convergent Total Synthesis of Ixabepilone and Its Analogues Enabled by Highly Efficient Asymmetric Hydrogenations
Li, Dong
Yan, Hao
Zong, Yan
Xiao, Renwei
Li, Shuo
Xia, Haidong
Zhang, Yao
Duan, Ya-Nan
Chen, Gen-Qiang
Zhang, Xumu
CHEMISTRY-A EUROPEAN JOURNAL, 2025, 31 (13)
[45] An Asymmetric Approach towards (-)-Aphanorphine and Its Analogues
Donets, Pavel A.
Goeman, Jan L.
Van der Eycken, Johan
Robeyns, Koen
Van Meervelt, Luc
Van der Eycken, Erik V.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (06) : 793 - 796
[46] Asymmetric synthesis and study of glutamate analogues.
Burkhart, DJ
McKenzie, AR
Myers, KI
Zhao, X
Magnusson, KR
Natale, NR
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2004, 228 : U919 - U920
[47] Asymmetric synthesis of phosphonic acid analogues for acylcarnitine
Yamagishi, T
Fujii, K
Shibuya, S
Yokomatsu, T
TETRAHEDRON, 2006, 62 (01) : 54 - 65
[48] Five-component synthesis of marimastat analogues
Patel, S
Saroglou, L
Floyd, CD
Miller, A
Whittaker, M
TETRAHEDRON LETTERS, 1998, 39 (45) : 8333 - 8334
[49] Synthesis of pyrrolostatin and its analogues
Fumoto, Y
Eguchi, T
Uno, H
Ono, N
JOURNAL OF ORGANIC CHEMISTRY, 1999, 64 (17): : 6518 - 6521
[50] Synthesis of (+)-vinblastine and its analogues
Miyazaki, Tohru
Yokoshirna, Satoshi
Simizu, Siro
Osada, Hiroyuki
Tokuyama, Hidetoshi
Fukuyama, Tohru
ORGANIC LETTERS, 2007, 9 (23) : 4737 - 4740

← 1 2 3 4 5 →