New approaches to the synthesis of trans-alkene isosteres of dipeptides

A Spaltenstein, PA Carpino, F Miyake…

Index: Spaltenstein, Andreas; Carpino, Philip A.; Miyake, Fumio; Hopkins, Paul B. Journal of Organic Chemistry, 1987 ,  vol. 52,  # 17  p. 3759 - 3766

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Citation Number: 75

Abstract

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 ...