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  • Title: A versatile enantioselective synthesis of barrenazines.
    Author: Peña-López M, Martínez MM, Sarandeses LA, Sestelo JP.
    Journal: Org Lett; 2010 Feb 19; 12(4):852-4. PubMed ID: 20092355.
    Abstract:
    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 C(2)-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.
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