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Synthesis and Transformation of (-)-Isopulegol-Based Chiral

Synthesis and Transformation of (-)-Isopulegol-Based Chiral

Tam Minh Le, Péter Bérdi, István Zupkó, Ferenc Fülöp, Zsolt Szakonyi

Int J Mol Sci. 2018 Nov 8;19(11):3522.

PMID: 30413128

Abstract:

A library of isopulegol-based β-amino acid derivatives has been developed from commercially-available (-)-isopulegol. Michael addition of primary and secondary amines towards α,β-unsaturated γ-lactones was accomplished resulting in β-aminolactones in highly-stereoselective reactions. Ring-opening of β-aminolactones with different amines furnished excellent yields of β-aminoamides. Moreover, the applicability of aminolactones in peptide synthesis was examined by opening the lactone ring with α- and β-aminoesters, providing dipeptides as promising chiral substrates for the synthesis of foldamers. The antiproliferative activities of β-aminolactones and β-aminoamides were explored, and the structure-activity relationships were studied from the aspects of the stereochemistry of the monoterpene ring and the substituent effects on the β-aminoamide ring system. The N-unsubstituted (-)-isopulegol-based β-aminoamides exhibited considerable antiproliferative activity against a panel of human adherent cancer cell lines (HeLa, MCF7 and MDA-MB-231).

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP104870566	(+)-Isopulegol		104870-56-6	Price

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