Recent Advances in Sustainable Total Synthesis and Chiral Pool Strategies with Emphasis on (−)‐Sclareol in Natural Products Synthesis

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC European Journal of Organic Chemistry Pub Date : 2025-02-24 DOI:10.1002/ejoc.202400983
Ayyoub Selka , Abdelnasser Abidli , Lucie Schiavo , Loïc Jeanmart , Gilles Hanquet , William D. Lubell
{"title":"Recent Advances in Sustainable Total Synthesis and Chiral Pool Strategies with Emphasis on (−)‐Sclareol in Natural Products Synthesis","authors":"Ayyoub Selka ,&nbsp;Abdelnasser Abidli ,&nbsp;Lucie Schiavo ,&nbsp;Loïc Jeanmart ,&nbsp;Gilles Hanquet ,&nbsp;William D. Lubell","doi":"10.1002/ejoc.202400983","DOIUrl":null,"url":null,"abstract":"<div><div>Starting materials for sustainable total synthesis often come from the chiral pool: carbohydrates, cyclitols, amino acids, and terpenes. In the terpene family, (−)‐sclareol has served as a sustainable, readily available, and versatile chiral building block for the synthesis of numerous natural products. (−)‐Sclareol possesses a unique structure that has consequently promoted its integration as a core framework within various structurally complex and biologically active substances, including sesquiterpenoids, diterpenoids, and sesterterpenoids. (−)‐Sclareol has facilitated access to diverse synthetic key intermediates, promoting the sustainable synthesis of several natural products. Herein, a review is presented covering the recent trends in sustainable total syntheses and the application of chiral pool approaches with emphasis on the preparation of natural products through diverse routes employing (−)‐sclareol as chiral educt. Innovative catalytic and synthetic protocols using (−)‐sclareol are also analyzed and discussed.</div></div>","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":"28 8","pages":"Article e202400983"},"PeriodicalIF":2.5000,"publicationDate":"2025-02-24","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ejoc.202400983","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S1434193X25000945","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

Starting materials for sustainable total synthesis often come from the chiral pool: carbohydrates, cyclitols, amino acids, and terpenes. In the terpene family, (−)‐sclareol has served as a sustainable, readily available, and versatile chiral building block for the synthesis of numerous natural products. (−)‐Sclareol possesses a unique structure that has consequently promoted its integration as a core framework within various structurally complex and biologically active substances, including sesquiterpenoids, diterpenoids, and sesterterpenoids. (−)‐Sclareol has facilitated access to diverse synthetic key intermediates, promoting the sustainable synthesis of several natural products. Herein, a review is presented covering the recent trends in sustainable total syntheses and the application of chiral pool approaches with emphasis on the preparation of natural products through diverse routes employing (−)‐sclareol as chiral educt. Innovative catalytic and synthetic protocols using (−)‐sclareol are also analyzed and discussed.

Abstract Image

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
以天然产品合成中的 (-)-Sclareol 为重点的可持续全合成和手性池策略的最新进展
可持续全合成的起始材料通常来自于手性:碳水化合物、环醇、氨基酸和萜烯。在萜烯家族中,(-)- sclareol是一种可持续的、容易获得的、多功能的手性构建块,用于合成许多天然产物。(-) - Sclareol具有独特的结构,因此促进了其作为各种结构复杂和生物活性物质(包括倍半萜、二萜和酯萜)的核心框架的整合。事实上,(-)‐sclareol促进了多种合成关键中间体的获取,促进了几种天然产物的可持续合成。本文对可持续全合成和手性池方法的最新趋势进行了批判性和全面的综述,重点介绍了利用(-)-核甾醇作为手性衍生物通过多种合成途径合成天然产物的方法。此外,本文还对近年来新开发的以(-)-核戊醇为底物的催化剂和合成方法进行了分析和讨论。
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
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
期刊最新文献
Blue-light-driven iron-catalyzed desulfurization of thioamides under hydrosilylation conditions Temperature-Dependent Regiodivergent Synthesis of Functionalized Maleimides and Itaconimides via in-situ Generated Pyridinium Ylide Photocarboxylation of Arylated 2H-Azirines Exploiting Continuous Flow Technology Recent Advances in Sustainable Total Synthesis and Chiral Pool Strategies with Emphasis on (−)‐Sclareol in Natural Products Synthesis Use of Real‐Time In‐Situ UV‐vis Spectrophotometry as a Tool for Monitoring Electrochemically‐Mediated Organic Synthesis
×
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