Journal of Organic Chemistry p. 4682 - 4693 (1988)
Update date:2022-08-03
Topics:
Wilson, Stephen R.
Zucker, Paul A.
The 1,4-diene unit is a key structural feature of many fatty acid derived natural products including arachidonic acid, several of the leukotrienes, and a variety of insect pheromones.In this paper substituted <2-<(trimethylsilyl)methyl>cyclopropyl>carbinols are demonstrated to cleave redily, upon treatment with acid or upon conversion to the corresponding mesylates, to give mono- and disubstituted 1,4-pentadienes.Stereoselective formation of cis and trans olefins from diastereomeric carbinols has been examined.Control of configuration at the olefin derived from the trimethylsilyl-bearing terminus of the cyclopropane system was found to be only moderate while the olefin derived from the carbinol terminus of the cyclopropane system was produced with high trans stereoselectivity.From these results it is concluded that the cleavage of the cyclopropane ring is neither significantly accelerated by, nor strongly coupled to, cleavage of the carbon-silicon bond.The high stereoselectivity observed for the formation of the trans configuration at the olefin derived from the carbinol terminus has been applied to the synthesis of a constituent of the melon fly pheromone.
View MoreZhenjiang Haitong Chemical Industry Co., Ltd.
Contact:+86 (511) 8448-0369
Address:Baoyan Town, Dantu District, Zhenjiang City, Jiangsu, China
Contact:(1) 206-3550089
Address:5115 NE 8TH PL, Renton, WA 98059 USA
Contact:+86-021-50792271
Address:Building 24A, 300 Chuantu Road, Chuansha, Pudong new area, Shanghai, China, 201202
Shaanxi Lighte Optoelectronics Material Co., Ltd.
Contact:+86-29-88320728-622/619/620
Address:No.55 INDUSTRY ROAD 2,XI'AN NATIONAL CIVIL AEROSPACE INDUSTRIAL PARK.XI'AN China 710065.
FOSHAN NANHAI ZHONGNAN PHARMACEUTICAL FACTORY
Contact:0086-0757-85609331
Address:XIAHENGTIAN INDUSTRIAL ZONE,SHAYONG VILLAGE,LISHUI TOWN
Doi:10.1080/07315171.2014.964791
(2015)Doi:10.1134/S1070428018070047
(2018)Doi:10.1002/hlca.19360190116
(1936)Doi:10.1007/s10562-018-2580-4
(2019)Doi:10.1039/jr9390001017
(1939)Doi:10.1039/c39880000272
(1988)