ChemInform Abstract: The First Example of an Intramolecular Diels—Alder Furan (IMDAF) Reaction of Iminium Salts and Its Application in a Short and Simple Synthesis of the Isoindolo[1,2‐a]isoquinoline Core of the Jamtine and Hirsutine Alkaloids.

Abstract

2-a]isoquinoline Core of the Jamtine and Hirsutine Alkaloids. -N-Alkylation of isoquinoline derivatives with alkyl halides affords intermediate iminium salts, which undergo unexpected spontaneous intramolecular Diels-Alder reaction to produce cycloadducts with the basic structural core of the title alkaloids. -(ZUBKOV*, F. I.; ERSHOVA, J. D.; ZAYTSEV, V. P.; OBUSHAK, M. D.; MATIYCHUK, V. S.; SOKOLOVA, E. A.; KHRUSTALEV, V. N.; VARLAMOV, A. V.; Tetrahedron Lett. 51 (2010) 52, 6822-6824, http://dx.