Journal of Organic Chemistry p. 2380 - 2390 (1990)
Update date:2022-08-02
Topics:
Piers, Edward
Gavai, Ashvinikumar V.
Transmetalation of (Z)-5-chloro-3-trimethylstannyl-2-pentene (8) with MeLi in tetrahydrofuran (THF) at -78 deg C provides the novel bifunctional reagent (E)-5-chloro-3-lithio-2-pentene (11), which can be transformed readily into the Grignard reagent (12).Copper(I)-catalyzed conjugate addition of (12) to cyclic α,β-unsatured ketones (e.g., 23-29), followed by intramolecular alkylation of the resultant chloro ketones (e.g., 30-36), affords the corresponding (Z)-ethylidenecyclopentane annulation products (e.g., 37-43).This new annulation method played a key role intotal syntheses of the sesquiterpenoids (+/-)-anhydrooplopanone (51), (+/-)-oplopanone (50), and (+/-)-8-epi-oplopanone (70).
View MoreSHENYANG COMEBOARD TECHNOLOGY CO., LTD
Contact:+86-24-25724626
Address:Room2210,Tianbao International Building,No.8-1 Weigong South Street,Tiexi District,Shenyang,China
Contact:+86-571-87010026
Address:202, Zhenhua Road,
Fujian Huitian Biological Pharmacy Co., Ltd.
Contact:0086-598-8300831; 8339920
Address:No.46,Taijiang Road,Sanming City,Fujian,China
Suzhou HeChuang Chemical Co.,Ltd.
Contact:+86-512-88800520
Address:No.9 Guanchao Rd,Changshu Advanced Materials Industy Park
Changyi Xinxing Technology Development Co., Ltd.
Contact:0086-510-86651065(Time Zone:8),86651656
Address:94 Yingbinxilu WestRoad, Huangtu Town, Jiangyin City, Jiangsu, China
Doi:10.1016/j.ica.2017.04.018
(2017)Doi:10.1016/j.bmcl.2005.05.133
(2005)Doi:10.1016/S0040-4039(00)86027-X
(1983)Doi:10.1016/j.apcata.2010.05.005
(2010)Doi:10.1016/j.tet.2005.07.124
(2006)Doi:10.1021/ja01115a017
(1953)
