摘要
以2-甲基-3-硝基苯胺为起始原料,经Batcho-Leimgruber、酰化、还原、氧化、R)-叔丁基亚磺酰胺的不对称诱导、烯烃闭环复分解反应等关键步骤,共经12步反应合成了麦角新碱中间体(S)-4-溴-3-{[5-(甲氧基羰基)-1-甲基-1,2,3,6-四氢吡啶-2-基]甲基}-1H-吲哚-1-甲酸叔丁酯,总收率7. 2%,该路线涉及4个新化合物的合成,其结构经~1H NMR,^(13)C NMR和MS(ESI)表征。
The key intermediate of ergometrine,tert-butyl-( S)-4-bromo-3-(( 5-( methoxycarbonyl)-1-methyl-1,2,3,6-tetrahydropyridin-2-yl) methyl)-1H-indole-1-carboxylate,was synthesized by 12 steps reaction from 2-methyl-3-nitroaniline,via Batcho-Leimgruber,acylation,reduction,oxidation,( R)-tert-butyl sulfonamide asymmetric induction,olefin ring closure metathesis and other key steps. The overall yield was 7. 2%. Four new compounds were involved in the synthetic route. The structures were characterized by 1H NMR,13C NMR and MS( ESI).
作者
郭振波
彭玉洁
权威
梁跃辉
王立升
GUO Zhen-bo;PENG Yu-jie;QUAN Wei;LIANG Yue-hui;WANG Li-sheng(College of Chemistry and Chemical Engineering,Guangxi University,Nanning 530004,China)
出处
《合成化学》
CAS
北大核心
2019年第1期31-34,68,共5页
Chinese Journal of Synthetic Chemistry
基金
国家自然科学基金资助项目(21262005)