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

IF 3.8 3区化学 Q2 CHEMISTRY, MULTIDISCIPLINARY

Frontiers in Chemistry Pub Date : 2024-10-11 eCollection Date: 2024-01-01 DOI:10.3389/fchem.2024.1477764

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

引用次数: 0

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.

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山口酯化：合成天然产物及其类似物的关键步骤--综述。

Yamaguchi 试剂基于 2,4,6-三氯苯甲酰氯 (TCBC) 和 4-二甲氨基吡啶 (DMAP)，是在合适的碱（Et3N 或 i Pr2NEt）和溶剂（THF、DCM 或甲苯）存在下进行酸和醇之间分子间（酯化）反应的有效工具。Yamaguchi 方案因其能够高效生产各种官能化酯、产率高、具有区域选择性、反应条件温和且反应时间短、易于操作而闻名。在此，我们回顾了山口试剂最近在合成大环内酯类、萜类、多酮类、肽类和代谢物等各种天然产物中的应用。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Frontiers in Chemistry Chemistry-General Chemistry

CiteScore

8.50

自引率

3.60%

发文量

1540

审稿时长

12 weeks

期刊介绍： Frontiers in Chemistry is a high visiblity and quality journal, publishing rigorously peer-reviewed research across the chemical sciences. Field Chief Editor Steve Suib at the University of Connecticut is supported by an outstanding Editorial Board of international researchers. This multidisciplinary open-access journal is at the forefront of disseminating and communicating scientific knowledge and impactful discoveries to academics, industry leaders and the public worldwide. Chemistry is a branch of science that is linked to all other main fields of research. The omnipresence of Chemistry is apparent in our everyday lives from the electronic devices that we all use to communicate, to foods we eat, to our health and well-being, to the different forms of energy that we use. While there are many subtopics and specialties of Chemistry, the fundamental link in all these areas is how atoms, ions, and molecules come together and come apart in what some have come to call the “dance of life”. All specialty sections of Frontiers in Chemistry are open-access with the goal of publishing outstanding research publications, review articles, commentaries, and ideas about various aspects of Chemistry. The past forms of publication often have specific subdisciplines, most commonly of analytical, inorganic, organic and physical chemistries, but these days those lines and boxes are quite blurry and the silos of those disciplines appear to be eroding. Chemistry is important to both fundamental and applied areas of research and manufacturing, and indeed the outlines of academic versus industrial research are also often artificial. Collaborative research across all specialty areas of Chemistry is highly encouraged and supported as we move forward. These are exciting times and the field of Chemistry is an important and significant contributor to our collective knowledge.