Tetrahedron p. 14603 - 14608 (1998)
Update date:2022-08-05
Topics:
Cominetti, Fulvio
Deagostino, Annamaria
Prandi, Cristina
Venturello, Paolo
Tetrahydrofurfuryl alcohol has been oxidized to the corresponding aldehyde (1) using TRAP and NMO. Subsequent Wittig reaction afforded 2-alk- 1-enyltetrahydrofurans (2 and 3) that can be metalated with Schlosser's reagent LICKOR. The base promotes the 1,4-eliminative ring fission, affording conjugate alkadien-1-ols (4 and 5) with high all E stereoselectivity. In the case of 2-pent-1-enyltetrahydrofuran, elimination reaction gives (4E,6E)- nona-4,6-dien-1-ol (5), which is structurally related to two sex pheromone components of the Caribbean fruit fly, Anastrepha suspensa.
View MoreContact:+86-025-52406782
Address:8 Taizishan Rd., Yanjiang Industrial Development Area, Nanjing, Jiangsu, China.
Shenyang Mole pharmaceutical Technology Development Co.,Ltd
Contact:+86-24-31204918/13889278616
Address:No.44, wanliutang road, shenhe District of Shenyang
Contact:+86-717-6370352
Address:168 Chengdong Avenue, Yichang, Hubei 443003, P. R.China
shanghai jinshan pharmaceutical Co.,Ltd
Contact:021-57363011,13681638167
Address:No. 7966 Tingfeng Road,Jinshan,Shanghai,China
ShiJiaZhuang Dowell Chemical Co.,Ltd.
website:http://www.dowechem.com
Contact:+86-13463963265,+86-311-89805679
Address:Xiyangling village, high tech Zone, Shijiazhuang,Hebei, China
Doi:10.1002/hlca.19840670133
(1984)Doi:10.1021/jo00168a039
(1983)Doi:10.1002/ardp.19813141012
(1981)Doi:10.1055/s-0035-1561202
(2016)Doi:10.1021/jo00201a023
(1985)Doi:10.1246/cl.1981.1605
(1981)