Enantiomeric Isopulegol As the Chiral Pool in the Total Synthesis of Bioactive Agents

Overview

Journal Chem Rec

Publisher Wiley

Specialty Chemistry

Date 2021 Sep 23

PMID 34553822

Citations 6

Authors

Tam Minh Le

Zsolt Szakonyi

Affiliations

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Abstract

Isopulegol, a pool of abundant chiral terpene, has long served as the starting material for the total synthesis of isopulegol-based drugs. As an inexpensive and versatile starting material, this compound continues to serve modern synthetic chemistry. This review highlights the total syntheses of terpenoids in the period from 1980 to 2020 in which with isopulegol applied as a building block.

Citing Articles

Bioinformatics Analysis of the Genome of IEGM 1362, an (-)-Isopulegol Biotransformer.

Maltseva P, Plotnitskaya N, Krivoruchko A, Beletskiy A, Rakitin A, Mardanov A Genes (Basel). 2024; 15(8).

PMID: 39202353 PMC: 11354180. DOI: 10.3390/genes15080992.

Synthesis and medicinal chemical characterisation of antiproliferative ,-functionalised isopulegol derivatives.

Le T, Njangiru I, Vincze A, Zupko I, Balogh G, Szakonyi Z RSC Adv. 2024; 14(26):18508-18518.

PMID: 38867736 PMC: 11168086. DOI: 10.1039/d4ra03467h.

Stereoselective Synthesis and Catalytical Application of Perillaldehyde-Based 3-Amino-1,2-diol Regioisomers.

Haznagy M, Csampai A, Ugrai I, Molnar B, Haukka M, Szakonyi Z Int J Mol Sci. 2024; 25(8).

PMID: 38673908 PMC: 11050431. DOI: 10.3390/ijms25084325.

Exploring the Chemical Space Accessed by Chiral Pool Terpenes. The (-)-Caryophyllene Oxide Paradigm.

Athanasiadou T, Bagkavou G, Karagianni P, Stathakis C Org Lett. 2024; 26(15):2897-2901.

PMID: 38552107 PMC: 11187627. DOI: 10.1021/acs.orglett.4c00132.

C-H Bonds as Functional Groups: Simultaneous Generation of Multiple Stereocenters by Enantioselective Hydroxylation at Unactivated Tertiary C-H Bonds.

Palone A, Casadevall G, Ruiz-Barragan S, Call A, Osuna S, Bietti M J Am Chem Soc. 2023; 145(29):15742-15753.

PMID: 37431886 PMC: 10651061. DOI: 10.1021/jacs.2c10148.