Synthesis of an eight-membered cyclic pseudo-dipeptide using ring closing metathesis.
Ring closing metathesis of diallylglycine 6 provided cyclic Z-olefin 7 in 80% yield. The reaction was promoted by substitution of the amide nitrogen with the 2,4-dimethoxybenzyl group allowing for the required cis diallylglycine amide rotamer. Removal of the protecting groups provided cyclic dipeptide 2, a constrained scaffold useful in peptidomimetic research.
The R. W. Johnson Pharmaceutical Research Institute, Welsh and McKean Roads, Spring House, Pennsylvania 19477, USA.
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Creighton
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Reitz
D000498:Allyl Compounds / Q000737:chemistry*; D004151:Dipeptides / Q000138:chemical synthesis / Q000737:chemistry*; D005998:Glycine / Q000031:analogs & derivatives / Q000737:chemistry*; D007202:Indicators and Reagents; D015394:Molecular Structure; D010456:Peptides, Cyclic / Q000138:chemical synthesis / Q000737:chemistry*
D000498:Allyl Compounds; D004151:Dipeptides; D007202:Indicators and Reagents; D010456:Peptides, Cyclic; C426410:diallylglycine; D005998:Glycine