Journal of Organic Chemistry 2002-08-23

Synthesis of the pro-gly dipeptide alkene isostere using olefin cross-metathesis.

Melissa M Vasbinder, Scott J Miller

Index: J. Org. Chem. 67(17) , 6240-2, (2002)

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Abstract

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.