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Paper | Special issue | Vol 93, No. 1, 2016, pp.114-126
Published online, 6th October, 2015
DOI: 10.3987/COM-15-S(T)7
Access to Apoerysopine and Pratosine Skeletons via Intramolecular Carbolithiation and Palladium-Catalyzed Alkenylation Reactions

Estíbaliz Coya, Esther Lete, and Nuria Sotomayor*

*Departamento de Química Orgánica, Facultad de Ciencia y Tecnologia, Universidad del País Vasco, Barrio Sarriena s/n. Leioa (Bizkaia) Bilbao 48940, Spain


(Pyrrolo[1,2-a]benzazepinyl)acetamides, obtained through carbolithiation reactions, have been used as intermediates in the access to Apoerysopine skeleton. Derivatization implies reduction to the correponding aldehyde using the Snieckus procedure for in situ generation of the Schwartz reagent, followed by Wittig reaction and intramolecular Pd(II)-catalyzed C-H alkenylation. The same sequence has been applied for the obtention of Pratosine from a pyrroloisoquinoline intermediate.