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Communication | Special issue | Vol 82, No. 1, 2010, pp.257-261
Published online, 9th April, 2010
DOI: 10.3987/COM-10-S(E)13
Spirocyclization of an N-Acyliminium Ion with Substituted Pyridine: Stereoselective Synthesis of Tetracyclic Spirolactams Possessing the Pyridone Nucleus

Hideki Abe, Kei-ichi Takaya, Kazuhiro Watanabe, Sakae Aoyagi,* Chihiro Kibayashi, and Tadashi Katoh*

*Department of Synthetic Organic Chemistry, Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Aoba-ku, Sendai 981-8558, Japan


An efficient method for the stereoselective synthesis of tetracyclic spirolactams was developed based on a spirocyclization of an N-acyliminium ion with 2-methoxypyridine as the aromatic π-nucleophile.