Journal of Organic Chemistry p. 3759 - 3766 (1987)
Update date:2022-07-29
Topics:
Spaltenstein, Andreas
Carpino, Philip A.
Miyake, Fumio
Hopkins, Paul B.
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.
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