A one-step synthesis of an aziridino mitosene analogue from 2-(N-phenylformimidoyl)indole
- 1 January 1983
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Chemical Communications
- No. 21,p. 1244-1245
- https://doi.org/10.1039/c39830001244
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.Keywords
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