Journal of Organic Chemistry p. 4929 - 4932 (1991)
Update date:2022-08-04
Topics:
Askin, D.
Verhoeven, T. R.
Liu, T. M.-H.
Shinkai, I.
An efficient process for the commercial preparation of the therapeutically important cholesterol lowering drug synvinolin (2: simvastatin, ZOCOR) from mevinolin (1: lovastatin, MEVACOR) is reported.The synthesis relies upon deactivation of the δ-lactone carbonyl toward enolization via conversion to the bis<(tert-butyldimethylsilyl)oxy>butylamide 7.An extremely high conversion (99.7percent) ester enolate alkylation of 7 affords 8 and 9.Subsequent desilylation and intramolecularly assisted basic amide hydrolysis in the presence of the dimethylbutyrate ester moiety yields 12, which is lactonized to 2.The overall yield from 1 to 2 is 86percent.
View MoreContact:+86-371-55981030
Address:Room 1571, Macalline Soho, No.1, Shangdu Road, Zhengzhou, Henan
Shanghai Massive Chemical Technology Co., Ltd.
website:http://www.massivechem.com/
Contact:+86 21 34943721
Address:Room 435, 4th floor, Building 9, No. 2568 Gudai Road,Minhang District, Shanghai,
Shanghai Bojing Chemical Co., Ltd.
Contact:021-37122233
Address:6F Buildiing 11,No.388,Baifu Road,District Fengxian.Shanghai, China.
Zhuzhou Farshine Chemical Industry Co., Ltd
Contact:0086-731-28482786
Address:No. 1,Shui Xian Road, He Tang Dictrict,Hunan-412000,China
Laizhou City Laiyu Chemical CO.,Ltd
Contact:+86-535-2719337/2719339
Address:Chenggang road zhuyou laizhou City Shangdong China
Doi:10.1016/S0040-4039(00)80824-2
(1988)Doi:10.1055/s-0029-1219557
(2010)Doi:10.1021/jo00286a032
(1989)Doi:10.1016/j.dyepig.2013.08.013
(2013)Doi:10.1021/jo00271a017
(1989)Doi:10.1021/ja9081815
(2009)