Journal of Organic Chemistry p. 10204 - 10213 (2016)
Update date:2022-08-17
Topics:
Tabuchi, Toshiki
Urabe, Daisuke
Inoue, Masayuki
The fused 6/7/5/6/6-membered (ABCDE) ring system of talatisamine was synthesized in 22 steps. After preparation of the AE-ring structure from 2-(ethoxycarbonyl)cyclohexanone, elaboration of the carboskeleton was realized by sequential additions of allyl magnesium bromide and the lithiated C-ring. The C11-bridgehead radical derived from the ACE-ring underwent the 7-endo cyclization with the enone moiety to form the B-ring in C10-stereoselective and C11-stereospecific manners. The 6-endo cyclization of the remaining D-ring was in turn attained by using the silyl enol ether as the nucleophile and the PhSeCl-activated olefin as the electrophile. These radical and cationic cyclizations were demonstrated to be highly chemoselective, and they significantly contributed to streamlining the route to the intricately fused pentacycle of talatisamine.
View MoreFusilin chemical science & technology co., ltd.
Contact:532-80698166/86057573, +86-400-669-7885
Address:School of Material Science & Engineering, Shandong Uinversity of Science & Technology, Huangdao Zone, Qindao, Shandong
Shanghai Pengkai Chemical Co.,Ltd
Contact:+86-21-60526671
Address:No.4226 Duzhuang Rd Minhang District Shanghai China
Suqian Ruixing Chemical Co., Ltd.
Contact:+86-527-80805666(总机);84836008(销售)
Address:3 Jingsilu, Zone north, Hubin Xincheng Development Park, Suqian, China
Nanjing Yuance Industry&Trade Co., Ltd.
website:http://www.njyuance.cn/
Contact:+86-25-85439097
Address:B1702, Aoti Bldg, No. 130, Aoti Avenue, Nanjing, China
Wuhan Silworld Chemical Co.,Ltd
website:http://www.silworldchemical.com
Contact:+86-27-85613400
Address:No.198 jiangjun Road, Wuhan,China 430033
Doi:10.1016/j.physc.2008.05.003
(2008)Doi:10.1002/anie.201912095
(2020)Doi:10.1021/acs.analchem.9b02427
(2019)Doi:10.1016/0040-4020(95)00906-X
(1996)Doi:10.1016/0031-9422(80)80221-4
(1980)Doi:10.1039/c19670000843
(1967)