Journal
AMINO ACIDS
Volume 41, Issue 3, Pages 597-608Publisher
SPRINGER WIEN
DOI: 10.1007/s00726-011-0891-5
Keywords
Beta-amino acid; Monoterpene; Chiral; Asymmetric synthesis; Chiral catalyst
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Funding
- Hungarian Research Foundation [OTKA NK81371, COST-CM0803, TAMOP-4.2.1/B-09/1/KONV-2010-0005-]
- Bolyai Janos Fellowships
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Natural monoterpenes have proved to be good starting materials for the synthesis of beta-amino acid derivatives. In the past decade, a number of well-known synthetic procedures have been applied for the preparation of monoterpene-based beta-amino acid derivatives, e.g. from beta-lactams via the 1,2-dipolar cycloaddition of chlorosulfonyl isocyanate to commercial or readily available monoterpenes [e.g. (+)- and (-)-alpha- or delta-pinene, (+)-3- and 2-carene, (+)- and (-)-apopinene], the conjugate addition of amides to monoterpene-based alpha,beta-unsaturated esters or the transformations of (-)-cis-pinonoic acid prepared by the oxidative cleavage of (+)- and (-)-verbenone. beta-Amino acid derivatives are excellent building blocks for versatile transformations, e.g. multicomponent reactions resulting in beta-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 beta-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 beta-aminocarboxamides, MDR inhibitor thiourea derivatives of beta-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 beta-amino acids and their derivatives.
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