460352-65-2Relevant academic research and scientific papers
Synthesis of the Pro-Gly Dipeptide Alkene Isostere Using Olefin Cross-Metathesis
Vasbinder, Melissa M.,Miller, Scott J.
, p. 6260 - 6263 (2007/10/03)
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.
