Tetrahedron p. 4458 - 4470 (2019)
Update date:2022-08-15
Topics:
Chen, Chien-Liang
Chiu, Tzu-Wei
Chen, Yung-Wen
Fang, Jim-Min
Influenza remains a health problem to humans. Peramivir is a FDA approved anti-influenza drug targeting the virus neuraminidase. The (3 + 2) cycloaddition reaction of 2-ethylbutanenitrile oxide with the cyclopentene dipolarophile derived from Vince lactam is a key step in the conventional synthesis of peramivir. Our study showed that conducting the (3 + 2) cycloaddition reactions with either aliphatic or aromatic nitrile oxide in hexane solution provided high percentage of the desired regioisomer, and the N-substituent having electron-withdrawing property is also beneficial to the regioselectivity. This study also demonstrated an alternative synthetic pathway of (?)-peramivir and the analog having a phenyl group in place of the 3-pentyl moiety.
View MoreXi'an caijing Opto-Electrical Science & Technology Co., LTD
Contact:+86-29-88294447
Address:NO.168 Zhangba Rd. East, Xi'an, P.R.China
Nantong Auxin Electronic Technology Co., LTD
Contact:86-513-88760026
Address:NO.5-1, Aoxin Road, Haian Hi-tech Development Zone, Jiangsu Province, China
Longhui qunfeng Chemical Co., Ltd
Contact:86-731-82173407
Address:South-east Industrial Park, Longhui County, Hunan Province, China
Contact:+86-717-6370352
Address:168 Chengdong Avenue, Yichang, Hubei 443003, P. R.China
Anhui Asahikasei Chemical Co., Ltd
Contact:86-551-4259770
Address:No. 88 Linquan Road Hefei Anhui China
Doi:10.1016/S0040-4039(01)93500-2
(1989)Doi:10.1246/bcsj.61.4476
(1988)Doi:10.1007/BF00605196
(1990)Doi:10.1021/jm00169a013
(1990)Doi:10.1021/jo00299a013
(1990)Doi:10.1021/jo50018a001
(1953)