Concise synthesis of (+/-)-horsfiline and (+/-)-coerulescine by tandem cyclisation of iodoaryl alkenyl azides.
A brief, efficient and economical synthesis of the spiropyrrolidinyloxindoles, horsfiline and coerulescine, has been achieved, starting from itaconic acid and, respectively, p-anisidine or o-iodoaniline. Tandem radical cyclisation of iodoaryl alkenyl azides is the key step in both syntheses.
Lizos
Dimitrios E
DE
Department of Pure and Applied Chemistry, University of Strathclyde, 295 Cathedral Street, Glasgow, Scotland, UK G1 1XL.
Murphy
John A
JA
D000475:Alkenes / Q000737:chemistry*; D000814:Aniline Compounds / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods; D009682:Magnetic Resonance Spectroscopy; D008956:Models, Chemical; D013141:Spiro Compounds / Q000138:chemical synthesis*; D013386:Succinates / Q000737:chemistry
D000475:Alkenes; D000814:Aniline Compounds; D013141:Spiro Compounds; D013386:Succinates; C480174:coerulescine; C443722:horsfiline; C013813:4-anisidine; C075715:3-iodoaniline; C005229:itaconic acid