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.
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Acknowledgments
We are grateful to the Hungarian Research Foundation (OTKA NK81371), COST-CM0803 and TÁMOP-4.2.1/B-09/1/KONV-2010-0005- for financial support and acknowledge the receipt of Bolyai János Fellowships for Zsolt Szakonyi.
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Szakonyi, Z., Fülöp, F. Monoterpene-based chiral β-amino acid derivatives prepared from natural sources: syntheses and applications. Amino Acids 41, 597–608 (2011). https://doi.org/10.1007/s00726-011-0891-5
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DOI: https://doi.org/10.1007/s00726-011-0891-5