新型(±)-反式二氢精氨酸类似物的立体选择性合成:含两个甲氧基取代基的关键中间体的制备

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY

Accounts of Chemical Research Pub Date : 2023-01-09 DOI:10.3311/ppch.20438

Balázs Lévai, Gábor Varró, A. Simon, L. Hegedűs, I. Kádas

{"title":"新型(±)-反式二氢精氨酸类似物的立体选择性合成:含两个甲氧基取代基的关键中间体的制备","authors":"Balázs Lévai, Gábor Varró, A. Simon, L. Hegedűs, I. Kádas","doi":"10.3311/ppch.20438","DOIUrl":null,"url":null,"abstract":"An efficient stereoselective synthesis of a pivotal intermediate, a cyclic allyl alcohol derivative containing two methoxy groups [(±)-22], using for the preparation of (±)-trans-dihydronarciclasine analogues was elaborated starting from easily available and inexpensive methyl gallate. This new synthetic route consists of 17 reaction steps, and provides an opportunity to obtain the wanted alkaloid derivative containing an additional methoxy group at position 11, in the ring A of the phenanthridone scaffold.","PeriodicalId":1,"journal":{"name":"Accounts of Chemical Research","volume":null,"pages":null},"PeriodicalIF":16.4000,"publicationDate":"2023-01-09","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"1","resultStr":"{\"title\":\"Stereoselective Synthesis of Novel (±)-trans-Dihydronarciclasine Analogues: Preparation of a Pivotal Intermediate Containing Two Methoxy Substituents\",\"authors\":\"Balázs Lévai, Gábor Varró, A. Simon, L. Hegedűs, I. Kádas\",\"doi\":\"10.3311/ppch.20438\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"An efficient stereoselective synthesis of a pivotal intermediate, a cyclic allyl alcohol derivative containing two methoxy groups [(±)-22], using for the preparation of (±)-trans-dihydronarciclasine analogues was elaborated starting from easily available and inexpensive methyl gallate. This new synthetic route consists of 17 reaction steps, and provides an opportunity to obtain the wanted alkaloid derivative containing an additional methoxy group at position 11, in the ring A of the phenanthridone scaffold.\",\"PeriodicalId\":1,\"journal\":{\"name\":\"Accounts of Chemical Research\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":16.4000,\"publicationDate\":\"2023-01-09\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"1\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Accounts of Chemical Research\",\"FirstCategoryId\":\"5\",\"ListUrlMain\":\"https://doi.org/10.3311/ppch.20438\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Accounts of Chemical Research","FirstCategoryId":"5","ListUrlMain":"https://doi.org/10.3311/ppch.20438","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}

引用次数: 1

摘要

本文以容易获得且价格低廉的没食子酸甲酯为原料，高效立体选择性合成了一种关键中间体，一种含有两个甲氧基[±)-22]的环烯丙醇衍生物，用于制备(±)-反式二氢精氨酸类似物。这种新的合成路线包括17个反应步骤，并提供了一个机会，以获得所需的生物碱衍生物含有一个额外的甲氧基在位置11，在非那恶酮支架的A环。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

查看原文本刊更多论文

Stereoselective Synthesis of Novel (±)-trans-Dihydronarciclasine Analogues: Preparation of a Pivotal Intermediate Containing Two Methoxy Substituents

An efficient stereoselective synthesis of a pivotal intermediate, a cyclic allyl alcohol derivative containing two methoxy groups [(±)-22], using for the preparation of (±)-trans-dihydronarciclasine analogues was elaborated starting from easily available and inexpensive methyl gallate. This new synthetic route consists of 17 reaction steps, and provides an opportunity to obtain the wanted alkaloid derivative containing an additional methoxy group at position 11, in the ring A of the phenanthridone scaffold.

求助全文

通过发布文献求助，成功后即可免费获取论文全文。去求助

来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.