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 Morewebsite:http://www.guarson.com
Contact:+86-523-88059600,+86-13805268803
Address:Room B1006,Yafang Building,Jiangyan Avenue,Jiangyan District, Taizhou City,Jiangsu,China
Nanjing Ruizhi Industry & Technologh Co.,Ltd.
Contact:+86-25-86808110
Address:441-4-A5,NO.12 Longzang Avenue,Yuhuatai District,210039,Nanjing
SHANXI JINJIN CHEMICAL INDUSTRIAL CO.,LTD
website:http://www.jinjingroup.com
Contact:4009982989
Address:Economic And Technological Development Zone,Hejin?City,Shanxi Province?,China
Shanghai Pengkai Chemical Co.,Ltd
Contact:+86-21-60526671
Address:No.4226 Duzhuang Rd Minhang District Shanghai China
Henan Yellow River New Material Technology Co.Ltd.
website:http://www.yellowriverchem.com
Contact:0086-373-7278760
Address:Chengguan Town, Yuanyang County
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)