Short and diverse route toward complex natural product-like macrocycles.
[reaction: see text] A general strategy toward macrocyclic compounds using multicomponent reaction (MCR) chemistry, e.g., Passerini and Ugi variants, and ring-closing metathesis (RCM) is introduced. The corresponding bifunctional isocyanides carboxylic acids bearing a terminal olefin are easy to prepare from the corresponding commercially available starting materials. Advantageously, this strategy allows fast access to a diverse conformational space of natural product-like macrocycles and could thus be of interest in the discovery of novel bioactive agents.
Beck
Barbara
B
Morphochem AG, Gmunderstr. 37-37a, 81379 München, Germany.
Larbig
Gregor
G
Mejat
Beatrice
B
Magnin-Lachaux
Marina
M
Picard
Anne
A
Herdtweck
Eberhardt
E
Dömling
Alexander
A
D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry; D001685:Biological Factors / Q000737:chemistry*; D002264:Carboxylic Acids / Q000138:chemical synthesis / Q000737:chemistry; D003486:Cyanides / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D046911:Macromolecular Substances; D008958:Models, Molecular; D015394:Molecular Structure
D000475:Alkenes; D001685:Biological Factors; D002264:Carboxylic Acids; D003486:Cyanides; D046911:Macromolecular Substances