{"title":"First total synthesis of Macrotricolorin A and its enantiomer.","authors":"Prakash Gupta Tanguturi, Balraju Gangapuram, Chinna Ashalu Kashamalla, Jhillu Singh Yadav","doi":"10.1080/14786419.2024.2341289","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, we demonstrate the first total synthesis of Macrotricolorin A <b>(1)</b> and its enantiomer <b>1'</b> from the key intermediate which is accessible from two precursors phenol and resorcinol, by two different sequences. Macrotricolorin A <b>(1)</b> possesses anti-inflammatory properties and is a novel diarylpropanoid. The first total synthesis of Macrotricolorin A <b>(1)</b> was accomplished using simple reactions such as Williamson's etherification, Claisen-Schmidt condensation, reduction, and chiral resolution.</p>","PeriodicalId":18990,"journal":{"name":"Natural Product Research","volume":" ","pages":"4428-4436"},"PeriodicalIF":1.6000,"publicationDate":"2025-08-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Natural Product Research","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1080/14786419.2024.2341289","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/5/2 0:00:00","PubModel":"Epub","JCR":"Q3","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
Herein, we demonstrate the first total synthesis of Macrotricolorin A (1) and its enantiomer 1' from the key intermediate which is accessible from two precursors phenol and resorcinol, by two different sequences. Macrotricolorin A (1) possesses anti-inflammatory properties and is a novel diarylpropanoid. The first total synthesis of Macrotricolorin A (1) was accomplished using simple reactions such as Williamson's etherification, Claisen-Schmidt condensation, reduction, and chiral resolution.
在此,我们展示了首次从关键中间体全合成巨三色堇素 A (1) 及其对映体 1'的过程,该中间体可通过两种不同的序列从苯酚和间苯二酚两种前体中获得。Macrotricolorin A (1) 具有抗炎特性,是一种新型二元丙醇类化合物。通过威廉姆森乙醚化、克莱森-施密特缩合、还原和手性解析等简单反应,首次完成了巨三色堇 A (1) 的全合成。
期刊介绍:
The aim of Natural Product Research is to publish important contributions in the field of natural product chemistry. The journal covers all aspects of research in the chemistry and biochemistry of naturally occurring compounds.
The communications include coverage of work on natural substances of land and sea and of plants, microbes and animals. Discussions of structure elucidation, synthesis and experimental biosynthesis of natural products as well as developments of methods in these areas are welcomed in the journal. Finally, research papers in fields on the chemistry-biology boundary, eg. fermentation chemistry, plant tissue culture investigations etc., are accepted into the journal.
Natural Product Research issues will be subtitled either ""Part A - Synthesis and Structure"" or ""Part B - Bioactive Natural Products"". for details on this , see the forthcoming articles section.
All manuscript submissions are subject to initial appraisal by the Editor, and, if found suitable for further consideration, to peer review by independent, anonymous expert referees. All peer review is single blind and submission is online via ScholarOne Manuscripts.