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Synthesis of highly functionalized phenylalanine derivatives via cross-enyne metathesis reactions

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
58
Issue
45
Identifiers
DOI: 10.1016/s0040-4020(02)01178-x
Keywords
  • Amino Acids And Derivatives
  • Metathesis
  • Dienes
  • Diels–Alder Reaction

Abstract

Abstract A new method for the synthesis of constrained phenylalanine derivatives is described. In this regard, the simple synthesis of acyclic diene building blocks embodying an α-amino acid moiety has been achieved. The diene building blocks have been prepared by cross enyne-metathesis reaction as a key step. The Diels–Alder reaction of the dienes with a dienophile such as dimethyl acetylenedicarboxilate (DMAD) followed by oxidation of the resulting cycloadduct gave highly substituted phenylalanine derivatives.

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