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

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

JOURNAL=Frontiers in Chemistry

VOLUME=12

YEAR=2024

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2024.1477764

DOI=10.3389/fchem.2024.1477764

ISSN=2296-2646

ABSTRACT=<p>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 (Et<sub>3</sub>N or <sup><italic>i</italic></sup>Pr<sub>2</sub>NEt) 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.</p>