Using cross-metathesis to couple L-phenylalanine to a macrocyclic lactam.
Grubbs' second generation ruthenium catalyst was used to couple the amino acid l-phenylalanine to a 17-membered lactam, using cross-metathesis with an E-alkene favored in the process. The best coupling conditions gave the product in 48% yield. The reversibility of the process was also confirmed. Ring-closing metathesis was a key reaction used to form the macrocyclic lactam.
Enholm
Eric
E
Department of Chemistry, University of Florida, Gainesville, Florida 32611, USA. enholm@chem.ufl.edu
Low
Tammy
T
D002384:Catalysis; D047029:Lactams, Macrocyclic / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D010649:Phenylalanine / Q000737:chemistry*; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D047029:Lactams, Macrocyclic; D010649:Phenylalanine; D012428:Ruthenium