Yamaguchi esterification: a key step toward the synthesis of natural products and their analogs-a review

Ramsha Munir; Ameer Fawad Zahoor; Muhammad Naveed Anjum; Asim Mansha; Ali Irfan; Aijaz Rasool Chaudhry; Ahmad Irfan; Katarzyna Kotwica-Mojzych; Mariola Glowacka; Mariusz Mojzych

doi:10.3389/fchem.2024.1477764

Yamaguchi esterification: a key step toward the synthesis of natural products and their analogs-a review

Front Chem. 2024 Oct 11:12:1477764. doi: 10.3389/fchem.2024.1477764. eCollection 2024.

Affiliations

¹ Department of Chemistry, Government College University Faisalabad, Faisalabad, Pakistan.
² Department of Applied Chemistry, Government College University Faisalabad, Faisalabad, Pakistan.
³ Department of Physics, College of Science, University of Bisha, Bisha, Saudi Arabia.
⁴ Department of Chemistry, College of Science, King Khalid University, Abha, Saudi Arabia.
⁵ Department of Basic Sciences, Department of Histology, Embriology and Cytophysiology, Medical University of Lublin, Lublin, Poland.
⁶ Faculty of Health Sciences Collegium Medicum, The Mazovian Academy in Plock, Płock, Poland.

Abstract

The Yamaguchi reagent, based on 2,4,6-trichlorobenzoyl chloride (TCBC) and 4-dimethylaminopyridine (DMAP), is an efficient tool for conducting the intermolecular (esterification) reaction between an acid and an alcohol in the presence of a suitable base (Et₃N or ⁱ Pr₂NEt) and solvent (THF, DCM, or toluene). The Yamaguchi protocol is renowned for its ability to efficiently produce a diverse array of functionalized esters, promoting high yields, regioselectivity, and easy handling under mild conditions with short reaction times. Here, the recent utilization of the Yamaguchi reagent was reviewed in the synthesis of various natural products such as macrolides, terpenoids, polyketides, peptides, and metabolites.

Keywords: Yamaguchi esterification; macrolides; metabolites; peptides; polyketides; terpenoids.

Publication types

Review

Grants and funding

The author(s) declare that financial support was received for the research, authorship, and/or publication of this article. The research was partly financed by the following research projects: Collegium Medicum, the Mazovian Academy in Plock, and Medical University of Lublin (DS 730). A. Irfan acknowledges the Deanship of Research and graduate studies at King Khalid University for funding this work through the Large Groups Research Project under grant number RGP2/156/45.