Russian Chemical Bulletin p. 1593 - 1597 (1993)
Update date:2022-07-29
Topics:
Chrelashvili, Z. G.
Mavrov, M. V.
Ugrak, B. I.
Kutin, A. A.
Serebryakov, E. P.
Two analogous routes to the title pheromones were elaborated based on organocuprate cross-coupling of Z,Z-dienic electrophiles, (2Z,4Z)-1-acetoxy-2,4-heptadiene (6) and (3Z,5Z)-1-bromoctadiene (8), with ω-tert-butoxy-1-chloropentane and -butane, respectively.Optimal conditions for the reaction of 2,4-heptadiyn-1-ol and 3,5-octadiyn-1-ol to the respective Z,Z-alkadienols as precursors for the electrophiles were found.Treatment of diynols with activated zinc in aqueous alcohol provided high geometrical purity of the product (> 94percent).In both cases, copper-catalyzed cross-coupling afforded 1-tert-butoxy-7,9-dodecadiene (four stereoisomers), acetolysis of which gave the target pheromone contaminated by stereoisomers.In the case of allylic electrophile 6, the reaction occured with the loss of the initial configurational purity, whereas the use of homoyllylic bromide 8 ensured almost complete retention of the configuration of the double bonds and obtaining the target pheromone of 87percent configurational purity.
View MoreBeijing ZhongDaXinHe Chemical Product Co.,Ltd(expird)
Contact:010-52876516
Address:tongzhoubeiyuan
SHANDONG AONA CHEMICAL CO.,LTD.
Contact:86-532-85762926
Address:LIUYUAN TOWN, ZAOZHUANG CITY, SHANGDONG PROVINCE.
SHANGHAI T&W PHARMACEUTICAL CO., LTD.
website:http://www.trustwe.com
Contact:+86-21-61551611
Address:601, No. 1, 2277 Nong, Zu Chongzhi Road, Zhangjiang Hightech. Park, Pudong
Taizhou YOJOY Chemical Co., Ltd.
Contact:13857143241
Address:Yangfu Industrial Park, Xianju, Zhejiang, P. R. China
Synochem Ingredients Corp., Ltd.
Contact:+86-512-5636 2180
Address:Zhangjiagang Free Trade Zone
Doi:10.1021/ja01534a056
(1958)Doi:10.1248/cpb.33.4034
(1985)Doi:10.1016/j.abb.2012.11.003
(2013)Doi:10.1016/j.tetlet.2014.01.076
(2014)Doi:10.1021/ol800028x
(2008)Doi:10.1002/ardp.19592920606
(1959)