A versatile enantioselective synthesis of barrenazines.

Peña-López, M.; Martínez, M. M.; Sarandeses, L. A.; Pérez Sestelo, J.


Org. Lett. 2010, 12, 852–854 (DOI: 10.1021/ol902920u).

Addition/Correction: Org. Lett. 2011, 13, 4151–4151 (DOI: 10.1021/ol201592g).

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A versatile enantioselective total synthesis of barrenazines A and B has been accomplished from 1,4-butanediol. The key steps of the synthesis are a sequential allylboration/ring-closing metathesis for the construction of the tetrahydropyridine ring and the preparation of a functionalized 4-azidopiperidin-5-one through a stereoselective epoxidation and regioselective ring-opening reaction. The C2-symmetrical pyrazine skeleton of barrenazines was prepared by dimerization of the azidopiperidinone, and the carbon side chain was completed by copper-catalyzed reactions using Grignard reagents.