Calothrixin B
Chemical Name: 12,13-Dihydro-7H-indolo[3,2-j]phenanthridine-7,13-dione
CAS No. 254114-34-6
项目整合开发状态: Biological Testing
项目研究机构: Australian National University (Originator)
合成路线:N-Protection of indole derivative (I) with methoxymethyl chloride (MOM-Cl) by means of NaH in THF provides aldehyde (II),which is converted into protected indolo-phenanthridine dione derivative (V) by coupling with quinoline (IV) by means of lithium tetramethylpiperidide (LiTMP) in THF (in turn,(IV) can be prepared from carboxylic acid (III) by treatment with thionyl chloride (SOCl2) and diethylamine (Et2NH)).Finally,the target compound is obtained by removal of the MOM group of (V) by treatment with aqueous HCl.
合成路线:N-Protection of indole derivative (I) with methoxymethyl chloride (MOM-Cl) by means of NaH in THF provides aldehyde (II),which is converted into protected indolo-phenanthridine dione derivative (V) by coupling with quinoline (IV) by means of lithium tetramethylpiperidide (LiTMP) in THF (in turn,(IV) can be prepared from carboxylic acid (III) by treatment with thionyl chloride (SOCl2) and diethylamine (Et2NH)).Finally,the target compound is obtained by removal of the MOM group of (V) by treatment with aqueous HCl,followed by selective oxidation of the pyridine nitrogen by means of m-CPBA.
📌 参考资料/链接：
参考文献标题:Synthesis of the potent antimalarials calothrixin A and B
文献作者:Kelly,T.R.; Zhao,Y.; Cavero,M.; Torneiro,M.
参考来源:Org Lett 2000,2(23),3735
📄 详细内容
合成路线:The methanolysis of anhydride (I) with dry refluxing methanol gives the monoester (II),which is treated with COCl2 to yield the acyl chloride (III).The condensation of (III) with indole (IV) by means of ZnCl2/MeMgCl and AlCl3 affords the adduct (V),which is N protected by means of Mom-Cl and NaH in THF to provide the intermediate (VI).The cyclization of (VI) by means of Temda and LiHMDS in THF gives the tetracyclic quinone (VII),which is finally deprotected with hot aq.HCl to provide the target Calothrixin B.
参考文献标题:A simple and concise route to calothrixin B
文献作者:Bernardo,P.H.; et al.
参考来源:Tetrahedron Lett 2002,43(16),2939
产品链接: CAS No. 254114-34-6››