A Stereocontrolled Synthesis of (+)-Febrifugine via Azide and Azide-Free Pathways.

IF 3.5 3区 化学 Q2 CHEMISTRY, MULTIDISCIPLINARY Chemistry - An Asian Journal Pub Date : 2025-01-14 DOI:10.1002/asia.202401579
Suwanan Uipanit, Kanyapat Lamyong, Sujitra Yakhampom, Boonsong Kongkathip, Paiboon Ngernmeesri, Nutthawat Chuanopparat
{"title":"A Stereocontrolled Synthesis of (+)-Febrifugine via Azide and Azide-Free Pathways.","authors":"Suwanan Uipanit, Kanyapat Lamyong, Sujitra Yakhampom, Boonsong Kongkathip, Paiboon Ngernmeesri, Nutthawat Chuanopparat","doi":"10.1002/asia.202401579","DOIUrl":null,"url":null,"abstract":"<p><p>(+)-Febrifugine, a natural antimalarial compound with a promising therapeutic profile, has become a hot target for synthetic chemists seeking to optimize its biological activity and expand its therapeutic applications. In this research, we present a stereocontrolled synthesis of (+)-febrifugine using both azide and azide-free approaches. Starting from the commercially available chiral pool precursor, d-glucose, the synthesis was completed in 20 steps for both approaches. Key reactions included the Zn-mediated Bernet-Vasella reaction, Horner-Wadsworth-Emmons reaction, and cyclization for constructing the chiral substituted piperidine ring. Additionally, α-bromoketone alkylation of quinazolinone was employed to assemble the (+)-febrifugine core structure.</p>","PeriodicalId":145,"journal":{"name":"Chemistry - An Asian Journal","volume":" ","pages":"e202401579"},"PeriodicalIF":3.5000,"publicationDate":"2025-01-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemistry - An Asian Journal","FirstCategoryId":"1","ListUrlMain":"https://doi.org/10.1002/asia.202401579","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

Abstract

(+)-Febrifugine, a natural antimalarial compound with a promising therapeutic profile, has become a hot target for synthetic chemists seeking to optimize its biological activity and expand its therapeutic applications. In this research, we present a stereocontrolled synthesis of (+)-febrifugine using both azide and azide-free approaches. Starting from the commercially available chiral pool precursor, d-glucose, the synthesis was completed in 20 steps for both approaches. Key reactions included the Zn-mediated Bernet-Vasella reaction, Horner-Wadsworth-Emmons reaction, and cyclization for constructing the chiral substituted piperidine ring. Additionally, α-bromoketone alkylation of quinazolinone was employed to assemble the (+)-febrifugine core structure.

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
通过叠氮化物和无叠氮化物途径立体控制合成(+)-Febrifugine。
(+)-Febrifugine是一种具有良好治疗前景的天然抗疟化合物,已成为合成化学家寻求优化其生物活性和扩大其治疗应用的热门靶点。在这项研究中,我们提出了一种立体控制合成(+)-热弗金使用叠氮化物和无叠氮化物的方法。从市售的手性池前体d-葡萄糖开始,两种方法的合成都需要20步。关键反应包括锌介导的Bernet-Vasella反应,Horner-Wadsworth-Emmons反应,以及构建手性取代哌啶环的环化反应。此外,采用α-溴酮烷基化的方法组装了(+)-苯基嘌呤核心结构。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
来源期刊
Chemistry - An Asian Journal
Chemistry - An Asian Journal 化学-化学综合
CiteScore
7.00
自引率
2.40%
发文量
535
审稿时长
1.3 months
期刊介绍: Chemistry—An Asian Journal is an international high-impact journal for chemistry in its broadest sense. The journal covers all aspects of chemistry from biochemistry through organic and inorganic chemistry to physical chemistry, including interdisciplinary topics. Chemistry—An Asian Journal publishes Full Papers, Communications, and Focus Reviews. A professional editorial team headed by Dr. Theresa Kueckmann and an Editorial Board (headed by Professor Susumu Kitagawa) ensure the highest quality of the peer-review process, the contents and the production of the journal. Chemistry—An Asian Journal is published on behalf of the Asian Chemical Editorial Society (ACES), an association of numerous Asian chemical societies, and supported by the Gesellschaft Deutscher Chemiker (GDCh, German Chemical Society), ChemPubSoc Europe, and the Federation of Asian Chemical Societies (FACS).
期刊最新文献
(Anti)aromaticity of cyclo[2n]carbons (n = 3 - 12). Advances in Metal-Free Transamidation: A Sustainable Approach to Amide Bond Formation. Advances in Transition-Metal-Catalyzed C(sp2)-H Bond Functionalization using Allyl Alcohols. Intramolecular Halogen Bonds Assist in Activating Carbonyl Groups for the Catalytic Synthesis of Bis(indolyl)methanes. Interface Engineering for High Strength and High Toughness Ceramic Matrix Composites.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1