在酸性条件下以脱芳为关键反应合成（±）-西蒙索尔C。

IF 2.2 4区化学 Q2 CHEMISTRY, ORGANIC

Beilstein Journal of Organic Chemistry Pub Date : 2025-03-17 eCollection Date: 2025-01-01 DOI:10.3762/bjoc.21.47

Xiao-Yang Bi, Xiao-Shuai Yang, Shan-Shan Chen, Jia-Jun Sui, Zhao-Nan Cai, Yong-Ming Chuan, Hong-Bo Qin

{"title":"在酸性条件下以脱芳为关键反应合成（±）-西蒙索尔C。","authors":"Xiao-Yang Bi, Xiao-Shuai Yang, Shan-Shan Chen, Jia-Jun Sui, Zhao-Nan Cai, Yong-Ming Chuan, Hong-Bo Qin","doi":"10.3762/bjoc.21.47","DOIUrl":null,"url":null,"abstract":"The total synthesis of (±)-simonsol C was accomplished using a dearomatization under acidic conditions as key step to construct an aryl-containing quaternary center. The 6/5/6 benzofuran unit was formed through reductive elimination with Zn/AcOH and a spontaneous oxy-Michael addition. This synthesis consists of 8 steps and achieves an overall yield of 13%, making it the shortest known route.","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"21 ","pages":"601-606"},"PeriodicalIF":2.2000,"publicationDate":"2025-03-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11931641/pdf/","citationCount":"0","resultStr":"{\"title\":\"Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions.\",\"authors\":\"Xiao-Yang Bi, Xiao-Shuai Yang, Shan-Shan Chen, Jia-Jun Sui, Zhao-Nan Cai, Yong-Ming Chuan, Hong-Bo Qin\",\"doi\":\"10.3762/bjoc.21.47\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"The total synthesis of (±)-simonsol C was accomplished using a dearomatization under acidic conditions as key step to construct an aryl-containing quaternary center. The 6/5/6 benzofuran unit was formed through reductive elimination with Zn/AcOH and a spontaneous oxy-Michael addition. This synthesis consists of 8 steps and achieves an overall yield of 13%, making it the shortest known route.\",\"PeriodicalId\":8756,\"journal\":{\"name\":\"Beilstein Journal of Organic Chemistry\",\"volume\":\"21 \",\"pages\":\"601-606\"},\"PeriodicalIF\":2.2000,\"publicationDate\":\"2025-03-17\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11931641/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Beilstein Journal of Organic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.3762/bjoc.21.47\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"2025/1/1 0:00:00\",\"PubModel\":\"eCollection\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.21.47","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/1/1 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}

引用次数: 0

摘要

以酸性条件下的脱芳反应为关键步骤，构建了含芳基的季中心，完成了（±）-西蒙索尔C的全合成。6/5/6苯并呋喃单元是通过Zn/AcOH还原消除反应和氧- michael自发加成反应形成的。该合成由8个步骤组成，总产率为13%，是已知最短的合成路线。

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

Total synthesis of (±)-simonsol C using dearomatization as key reaction under acidic conditions.

The total synthesis of (±)-simonsol C was accomplished using a dearomatization under acidic conditions as key step to construct an aryl-containing quaternary center. The 6/5/6 benzofuran unit was formed through reductive elimination with Zn/AcOH and a spontaneous oxy-Michael addition. This synthesis consists of 8 steps and achieves an overall yield of 13%, making it the shortest known route.

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

Beilstein Journal of Organic Chemistry 化学-有机化学

CiteScore

4.90

自引率

3.70%

发文量

167

审稿时长

1.4 months

期刊介绍： The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.