Synthesis of the pro-gly dipeptide alkene isostere using olefin cross-metathesis.
Melissa M Vasbinder, Scott J Miller
文献索引:J. Org. Chem. 67(17) , 6240-2, (2002)
全文:HTML全文
摘要
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.
相关化合物
相关文献:
2001-01-01
[J. Org. Chem. 61(22) , 7784-7792, (1996)]
The flash vacuum thermolysis of (-)-cocaine. Sisti NJ, et al.
[Tetrahedron Lett. 30(44) , 5977-80, (1989)]
Site of protonation in the chemical ionization mass spectra of olefinic methyl esters. Harrison AX and Ichikawa H.
[Org. Mass Spectrom. 15(5) , 244-48, (1980)]