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Building constrained peptidomimetics: A convenient approach to 3-phenyl-5-vinyl substituted proline derivatives


, : Building constrained peptidomimetics: A convenient approach to 3-phenyl-5-vinyl substituted proline derivatives. Tetrahedron 57(30): 6407-6415, 23 July

An approach to the synthesis of 3-phenyl-5-vinyl substituted prolines starting from readily available 2,3-disubstituted pentenoic acid derivatives is reported. The route converts the pentenoic acid derived starting materials into cyclic N-acyliminium ion precursors with the use of a hydroboration-Swern oxidation sequence. This overall transformation worked best when the initial alkylborane product was treated sequentially with excess MCPBA and then acetone prior to the Swern oxidation. In this way, a 70% yield of the desired N-acyliminium ion precursor could be obtained. Once in hand, the cyclic N-acyliminium ion precursor was used to make the desired 3-phenyl-5-vinyl substituted prolines.

US$19.90

DOI: 10.1016/s0040-4020(01)00532-4


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