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Note | Special issue | Vol 73, No. 1, 2007, pp.863-872
Published online, 3rd August, 2007
DOI: 10.3987/COM-07-S(U)21
Natural Product Inspired meta/para-Biaryl Ether Lactam Macrocycles by Double Ugi Multicomponent Reactions

Bernhard Westermann, Dirk Michalik, Angela Schaks, Oliver Kreye, Christoph Wagner, Kurt Merzweiler, and Ludger A. Wessjohann*

*Leibniz Institute of Plant Biochemistry, Department of Bioorganic Chemistry, Weinberg 3, 06120 Halle, Germany

Abstract

Isonitrile meta/para’-functionalized biaryl ethers can serve as key building blocks for the highly efficient and diverse one step production of natural product inspired peptide/peptoid macrocycles, thereby forming up to 54-membered rings with eight or even sixteen new bonds. Aliphatic diamine and diacid tethers give access to two different classes of biaryl ether cyclopeptoids, either with exo/endo or exclusively endo dipeptidic moieties.