Stereoselective Synthesis of (4Z,6E)-Dodecadien-1-al

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Chin. J. Org. Chem. ›› 2005, Vol. 25 ›› Issue (05): 558-560. Previous Articles Next Articles

Original Articles

松毛虫性信息素前体(4Z,6E)-十一碳二烯醛的合成

陶云海¹,2，程伟贤¹，黄相中¹，张玉顺¹，古昆*^,a,b

(¹云南大学化学与材料工程学院昆明 650091)
(²云南大学生物制药创新人才培养基地昆明 650091)

收稿日期:2004-05-07 修回日期:2004-11-23 发布日期:2004-04-30
通讯作者: 古昆

Stereoselective Synthesis of (4Z,6E)-Dodecadien-1-al

TAO Yun-Hai¹,2,CHENG Wei-Xian¹,HUANG Xiang-Zhong¹
ZHANG Yu-Shun¹,GU Kun*^,a,b

(Shool of Chemistry and Material, Yunnan University, Kunming 650091)
(Center for Ad-vanced Studies of Medical and Organic Chemistry, Yunnan University, Kunming 650091)

Received:2004-05-07 Revised:2004-11-23 Published:2004-04-30

Contact: GU Kun

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Abstract

Starting from acetylene, 7-bromo-(4Z,6E)-heptadien-1-al was stereoselectively synthesized by the tandem addition reaction of acrolein with acetylene. Stereoselective synthesis of (4Z,6E)-dodecadien-1-al was achieved via three steps including palladium-catalyzed coupling reaction from 7-bromo-(4Z,6E)- heptadien-1-al.

Key words: stereoselective synthesis, coupling-reaction, (4Z,6E)-dodecadien-1-ol

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TAO Yun-Hai^1,2,CHENG Wei-Xian,HUANG Xiang-Zhong
ZHANG Yu-Shun,GU Kun*^,a,b. Stereoselective Synthesis of (4Z,6E)-Dodecadien-1-al[J]. Chin. J. Org. Chem., 2005, 25(05): 558-560.

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[1]	Yangxing Sun, Yanzhi Li, Yanlai Cao, Nengzhong Wang, Shaohua Xiang, Mingguo Liu, Hui Yao. Research Advances in Functional Group-Directed Stereoselective Glycosylation [J]. Chinese Journal of Organic Chemistry, 2022, 42(11): 3506-3529.
[2]	Liao Fumin, Yu Jinsheng, Zhou Jian. Recent Advances in the Highly Stereoselective Synthesis of Tri-or Tetra-substituted Monofluoroalkenes [J]. Chin. J. Org. Chem., 2017, 37(9): 2175-2186.
[3]	Gao Yanjiao, Xiao Zhenhua, Liu Liangxian, Huang Peiqiang. Direct Reductive Cyanation of A 2-Pyrrolidinone Chiral Building Block Bearing An Unprotected Hydroxyl Group: A Stereoselective Synthesis of N-Methyl-2-epi-bulgecinine [J]. Chin. J. Org. Chem., 2017, 37(5): 1189-1197.
[4]	Yang Zhen, Jing Peng, She Xuegong. A Stereoselective Synthesis of the C(13)-C(23) Fragment of Iriomoteolide-1b [J]. Chin. J. Org. Chem., 2012, 32(02): 338-343 .
[5]	YANG Shu-Xin, CHEN Jie, WU Xiao-Yu, DENG Hong-Mei, SHAO Min, ZHANG Hui, CAO Wei-Guo. Facile, Highly Stereoselective Synthesis of Spiro[cyclopropane-1,3 - indolin]-2 -ones and Spiro[cyclopropane-1,2 -indane]-1 ,3 -diones Containing Trifluoromethyl Group [J]. Chin. J. Org. Chem., 2010, 30(10): 1521-1528.
[6]	XU Xiao-Bo, YANG Ying-Bin, DENG Qin, XIANG Li, XIANG Jian-Nan. Stereoselective Synthesis of 4-Acetoxyazetidione: the Key Intermediate of Penem and Carbapenem Antibiotics [J]. Chin. J. Org. Chem., 2010, 30(07): 1017-1020.
[7]	WANG Meng, ZHANG Hui, CHEN Jie, TUN Xiao-Tu, DENG Gong-Mei. Highly Stereoselective Synthesis of Spiro[cyclopropane-1,4'- pyrazolin-5'-one] Derivertives via Ammonium Ylide [J]. Chin. J. Org. Chem., 2009, 29(10): 1611-1616.
[8]	GENG, Xiao-Hong; ZHOU, Hui; CHEN, Pei-Ran* ; XU, Qing. Recent Advances in the Stereoselective Synthesis of α-Cyanohydrins [J]. Chin. J. Org. Chem., 2008, 28(07): 1157-1163.
[9]	LIU Gang^1,2,ZHANG Rong-Li,CAI Ming-Zhong*^,1. Synthesis and Catalytic Characteristics of a Silica-Supported Poly-ω-(methylseleno)undecylsiloxane Palladium(0) Complex [J]. Chin. J. Org. Chem., 2006, 26(02): 215-218.
[10]	ZHONG, Ping. Synthesis of Various Vinylzirconium Compounds and Their Application in Stereoselective Synthesis of Di- and Tri-substituted Alkenes [J]. Chinese Journal of Organic Chemistry, 2004, 24(4): 374-379.
[11]	ZENG Ji-Chao, LU Rui-Liang, XU Xin-Hua, FANG Jing-Kun, ZHOU Bing, ZHANG Qiu-Lin. Highly Selective Synthesis of (Z)-1,2-Bis(arylseleno)-1-alkenes via Addition of Diaryl Diselenides to Terminal Acetylenes Catalyzed by Cesium Hydroxide [J]. Chinese Journal of Organic Chemistry, 2004, 24(11): 1482-1484.