Tetrahedron

An access to (Z)-ethylenic pseudodipeptides based on ring-closing metathesis

V Boucard, H Sauriat-Dorizon, F Guibé

Index: Boucard, Valerie; Sauriat-Dorizon, Helene; Guibe, Francois Tetrahedron, 2002 ,  vol. 58,  # 36  p. 7275 - 7290

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Citation Number: 24

Abstract

A new access to enantiopure (Z)-ethylenic pseudopeptides, starting from the chiral pool of amino acids and enantiopure 2-substituted-but-3-enoic acids is proposed and illustrated by the syntheses of the (Z)-ethylenic pseudopeptidic analogs of l-Phe-l-Phe, l-Phe-d-Phe, l-Phe- l-Val, l-Phe-d-Val and racemic (ll, dd) and (ld, dl)(phenyl) Gly-Phe. The key-steps of these syntheses are a ring-closing metathesis, catalysed by Grubbs' ruthenium alkykidene ...