Multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs) based on Staudinger and Passerini three-component reactions.
Multiple multicomponent macrocyclizations including bifunctional buildings blocks (MiBs) so far have relied almost exclusively on Ugi reactions. The efficient expansion to non-Ugi-MiBs is exemplified by the synthesis of tetra-beta-lactam and bis-alpha-acyloxy carboxamide macrocycles based on multiple Staudinger and Passerini three-component reactions (3CR), respectively. A recent variation of the Passerini-3CR that involves primary alcohols, isocyanides, and carboxylic acids under oxidative conditions is successfully adapted to this procedure.
Leon
Fredy
F
Department of Bioorganic Chemistry, Leibniz Institute of Plant Biochemistry, Weinberg 3, D-06120 Halle/Saale, Germany.
Rivera
Daniel G
DG
Wessjohann
Ludger A
LA
D047028:Macrocyclic Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods*
D047028:Macrocyclic Compounds