Monoterpene-based chiral β-amino acid derivatives prepared from natural sources: Syntheses and applications

Research output: Contribution to journalArticle

32 Citations (Scopus)

Abstract

Natural monoterpenes have proved to be good starting materials for the synthesis of β-amino acid derivatives. In the past decade, a number of well-known synthetic procedures have been applied for the preparation of monoterpene-based β-amino acid derivatives, e.g. from β-lactams via the 1,2-dipolar cycloaddition of chlorosulfonyl isocyanate to commercial or readily available monoterpenes [e.g. (+)- and (-)-α- or δ-pinene, (+)-3- and 2-carene, (+)- and (-)-apopinene], the conjugate addition of amides to monoterpene-based α,β-unsaturated esters or the transformations of (-)-cis-pinonoic acid prepared by the oxidative cleavage of (+)- and (-)-verbenone. β-Amino acid derivatives are excellent building blocks for versatile transformations, e.g. multicomponent reactions resulting in β-lactams, syntheses of 1,3-heterocycles and diaminopyrimidine derivatives or the formation of peptides containing an H12 helix. 1,3-Amino alcohol derivatives prepared from β-amino esters have been applied as chiral catalysts in enantioselective transformations. Several of these compounds are of noteworthy pharmacological importance, such as tyrosine kinase Axl inhibitor diaminopyrimidine-coupled β-aminocarboxamides, MDR inhibitor thiourea derivatives of β-amino esters or 2-imino-1,3-oxazines, which exhibit marked growth inhibitory activity on multiple cancer cell lines. The present review summarizes recent developments relating to the syntheses, applications and pharmaceutical importance of monoterpene-based β-amino acids and their derivatives.

Original languageEnglish
Pages (from-to)597-608
Number of pages12
JournalAmino Acids
Volume41
Issue number3
DOIs
Publication statusPublished - Aug 1 2011

Keywords

  • Asymmetric synthesis
  • Beta-amino acid
  • Chiral
  • Chiral catalyst
  • Monoterpene

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

Fingerprint Dive into the research topics of 'Monoterpene-based chiral β-amino acid derivatives prepared from natural sources: Syntheses and applications'. Together they form a unique fingerprint.

  • Cite this