New Approaches to the Synthesis of trans-Alkene Isosteres of Dipeptides

Article abstract of DOI:10.1021/jo00226a007

Two new syntheses of protected dipeptide analogues bearing a trans carbon-carbon double bond in place of the amide linkage are reported.One route is a linear synthesis employing the rearrangement of an allylic selenide to a protected allylic amine.The second route is convergent and uses the Julia olefin synthesis in a key step.The latter route is fully stereocontrolled and has been used to prepare protected trans-alkene isosteres of the dipeptides TyrAla, PhePhe, LeuPhe, and LeuLeu.