Journal of Organic Chemistry p. 4920 - 4924 (1986)
Update date:2022-08-02
Topics:
Dirlam, John P.
Clark, David A.
Hecker, Scott J.
A convergent total synthesis of the antibiotic (+/-)-indolmycin (1) is presented.N-Carbobenzoxy-3-(1-chloroethyl)indole (12) is prepared in three steps from indole-3-carboxaldehyde (9).Alkylation of the lithium anion of 2-(dimethylamino)-4(5H)-oxazolone (4) with chloride (12) provides a mixture of the (+/-)-2-dimethylamino derivative of indolmycin (13) and its diastereomer (14) in a ratio of 2.2:1.Amine exchange is effected by treatment of 13 with methylamine, affording (+/-)-1 in five steps from commercially available 9.Efforts to extend this technology toward an asymmetric synthesis of (-)-1 are described.
View MoreAirsea(Taizhou) Pharmaceutical Limited(expird)
Contact:+86-576-88057622
Address:Dubei, Duqiao, Linhai, Taizhou, Zhejiang, China Zip: 317016
Changsha Kamer Essence and Flavor Co.,Ltd
Contact:86-731-89832270
Address:No.327 Kangnin Road Changsha Bio Information Industry Park, Changsha city, Hunan province
Pure Chemistry Scientific Inc.
Contact:+1-857-366-7588
Address:14905 SW freeway street #232, Sugarland, TX 77478, USA
Hangzhou Maytime Bio-Tech Co.,Ltd.
website:http://www.maytime.com.cn
Contact:+86-571-88925295 88920965
Address:NO.2-1701 Ganghui Central Ningwei Street, Xiaoshan Hangzhou Zhejiang China
Shanghai WinTide BioTechnology Co.,Ltd
Contact:86-21-37100630
Address:No. 908 Yunhe Road, Fengxian district, Shanghai
Doi:10.1021/ol005629l
(2000)Doi:10.1248/cpb.44.492
(1996)Doi:10.1021/ja065898s
(2006)Doi:10.1080/00397911.2010.488308
(2011)Doi:10.1021/jo00376a056
(1986)Doi:10.1016/j.bmcl.2008.06.014
(2008)
