CY-208-243
(-)-(6aR,12bR)-4,6,6a,7,8,12β-六氢-7-甲基吲哚[4,3-a]菲啶Chemical Name: (-)-trans-4,6,6a,7,8,12b-Hexahydro-7-methylindolo[4,3-ab]phenanthridine; (-)-(6aR,12bR)-7-Methyl-4,6,6a,7,8,12b-hexahydroindolo[4,3-ab]phenanthridine
CAS No. 100999-26-6
项目整合开发状态: Phase II
项目研究机构: Novartis (Originator)
合成路线:The condensation of 1-benzoyl-1,2,2a,3,4,5-hexahydrobenzo[c,d]indol-4-one (I) with methylamine followed by acylation of the resulting enamine with benzoyl chloride gives 1,N-dibenzoyl-4-(methylamino)-1,2,2a,3-tetrahydrobenzo[c,d]indole (II) which,by irradiation with UV light in acetone,is isomerized to (5aR*,6aS*,12bS*)-4-benzoyl-7-methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridin-8-one (III).The reduction of (III) with LiAlH4 in ether,followed by hydrolysis with NaOH,and optical resolution with (+)-mandelic acid affords (+)-(5aS,6aR,12bR)-7-methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridine (IV),which is finally dehydrogenated with MnO2 in methylene chloride.
📌 参考资料/链接：
参考文献标题:Indolophenanthidines,their preparation and use
文献作者:Hagenbach,A.; Seiler,M.P.; Whrich,H.J.(Novartis AG; Novartis Deutschland GmbH)
参考来源:DE 3402392; EP 0155903; ES 8606339; JP 1985197687; US 4634708
📄 详细内容
合成路线:The condensation of 1-benzoyl-1,2,2a,3,4,5-hexahydrobenzo[c,d]indol-4-one (I) with methylamine followed by acylation of the resulting enamine with benzoyl chloride gives 1,N-dibenzoyl-4-(methylamino)-1,2,2a,3-tetrahydrobenzo[c,d]indole (II) which,by irradiation with UV light in acetone,is isomerized to (5aR*,6aS*,12bS*)-4-benzoyl-7-methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridin-8-one (III).The reduction of (III) with LiAlH4 in ether,followed by hydrolysis with NaOH,and optical resolution with (+)-mandelic acid affords (+)-(5aS,6aR,12bR)-7-methyl-4,5,5a,6,6a,7,8,12b-octahydroindolo[4,3-ab]phenanthridine (IV),which is finally dehydrogenated with MnO2 in methylene chloride.
参考文献标题:CY-208-243
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1990,15(4),344
产品链接: CAS No. 100999-26-6››