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 MoreANHUI CHEM-BRIGHT BIOENGINEERING CO.,LTD
Contact:86-561-4080321
Address:No.8 Lieshan Industrial Zone of Huaibei
NINGBO YINLIANG FOREIGN TRADE CO., LTD.
Contact:+86-574-87834016 / 87898057
Address:23F NO.666JINYU ROAD,YINGZHOU DISTRICT,NINGBO.CHINA
SHENYANG COMEBOARD TECHNOLOGY CO., LTD
Contact:+86-24-25724626
Address:Room2210,Tianbao International Building,No.8-1 Weigong South Street,Tiexi District,Shenyang,China
NINGBO PANGS CHEM INT’L CO.,LTD.
Contact:+86-574-27666845
Address:FLOOR 21,BUILDING NO.11,XIN TIAN DI,NO.689 SHI JI ROAD,NINGBO CHINA
Contact:+49-4101-3053-0
Address:Waldhofstrasse 14 ,25474 Ellerbek Germany
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)
