DB-38

Chemical Name: 10-Amino-5-ethyl-5-hydroxy-12-(trimethylsilyl)-4,5,13,15-tetrahydro-1H,3H-oxepino[3',4':6,7]indolizino[1,2-b]quinoline-3,15-dione
项目整合开发状态: Biological Testing
项目研究机构: University of Kentucky (Originator), Tigen Pharmaceuticals (Codevelopment)
合成路线:The known enol ether (I) was dihydroxylated with OsO4 and then oxidatively cleaved to the keto formate (II) by means of Pb(OAc)4.Reformatskii reaction of (II) with (tert-butoxycarbonyl)methylzinc bromide gave hydroxyester (III).Further cyclization of (III) using trifluroacetic acid produced lactone (IV).Halogenation with iodine monochloride afforded iodopyridine (V).Then,cleavage of the methyl ether of (V) employing trimethylsilyl iodide generated the pyridone lactone (VI),which was N-alkylated with 3-(trimethylsilyl)propargyl bromide (VII),yielding (VIII).Radical annulation of (VIII) with isonitrile (IX) in the presence hexamethylditin furnished the pentacyclic system (X).Finally,removal of the N-Boc protecting group of (X) yielded the title compound.

合成路线:The known enol ether (I) was dihydroxylated with OsO4 and then oxidatively cleaved to the keto formate (II) by means of Pb(OAc)4.Reformatskii reaction of (II) with (tert-butoxycarbonyl)methylzinc bromide gave hydroxyester (III).Further cyclization of (III) using trifluroacetic acid produced lactone (IV).Halogenation with iodine monochloride afforded iodopyridine (V).Then,cleavage of the methyl ether of (V) employing trimethylsilyl iodide generated the pyridone lactone (VI),which was N-alkylated with 3-(tert-butyldimethylsilyl)propargyl bromide (VII),yielding (VIII).Finally,radical annulation of (VIII) with phenyl isonitrile (IX) in the presence hexamethylditin furnished the title pentacyclic compound.