A one-step synthesis of an aziridino mitosene analogue from 2-(N-phenylformimidoyl)indole
Abstract
1,1a,2,8b-Tetrahydro-1-phenyl-1a-(methoxycarbonyl)azirino[2′,3′ :3,4]pyrrolo[1,2-a]indole (4), containing the complete ring system of the mitomycin antitumour antibiotics, is formed in a single step from 2-(N-phenylformimidoyl)indole (2) by treatment of its sodium salt with methyl 2-bromopropenoate; the aziridine undergoes facile thermal ring-opening to an azomethine ylide which adds in situ to dimethyl butynedioate in 1,3-dipolar fashion.