Using cross-metathesis to couple L-phenylalanine to a macrocyclic lactam

The Journal of Organic Chemistry
Eric Enholm, Tammy Low

Abstract

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.

References

Feb 27, 2003·Journal of the American Chemical Society·Tina M TrnkaRobert H Grubbs
Oct 14, 2005·Journal of the American Chemical Society·Arnab K ChatterjeeRobert H Grubbs

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Citations

Jul 29, 2010·Journal of the American Chemical Society·Nicolaas A VermeulenM Christina White
Sep 11, 2010·International Journal of Urban and Regional Research·Ellen ReeseLeanne Thach
Mar 23, 2007·Organic & Biomolecular Chemistry·Thomas MorrisStephen Caddick

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