Synthesis of the pro-gly dipeptide alkene isostere using olefin cross-metathesis.
An approach to the synthesis of dipeptide olefin isosteres using intermolecular olefin cross-metathesis is presented. In particular, a synthesis of the Pro-Gly isostere (1) is reported. Conversion of N-BOC-proline into the corresponding vinyl-substituted carbamate provides the N-terminal cross-metathesis partner (2). Methyl 3-butenoate (3) is employed as the C-terminal component. Treatment of the two partners in an optimized molar ratio affords the cross product 1 (83% yield). Three other examples are demonstrated to evaluate the potential of the approach.
Department of Chemistry, Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3860, USA.
Melissa M
MM
Vasbinder
Scott J
SJ
Miller
D000475:Alkenes / Q000737:chemistry*; D002625:Chemistry, Organic / Q000379:methods*; D002855:Chromatography, Thin Layer; D004151:Dipeptides / Q000138:chemical synthesis*; D006033:Glycylglycine / Q000737:chemistry; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011392:Proline / Q000031:analogs & derivatives / Q000737:chemistry; D013237:Stereoisomerism
D000475:Alkenes; D004151:Dipeptides; D006033:Glycylglycine; C057749:prolylglycine; D011392:Proline