{"title":"Catalytic remodeling of complex alkenes to oxonitriles through C=C double bond deconstruction.","authors":"Zengrui Cheng, Kaimeng Huang, Chen Wang, Lili Chen, Xinyao Li, Zhibin Hu, Xinyuan Shan, Peng-Fei Cao, Haofeng Sun, Wei Chen, Chenhao Li, Ziyao Zhang, Hui Tan, Xue Jiang, Guikai Zhang, Zhongying Zhang, Min Lin, Liang Wang, Anmin Zheng, Changjiu Xia, Teng Wang, Song Song, Xingtian Shu, Ning Jiao","doi":"10.1126/science.adq8918","DOIUrl":null,"url":null,"abstract":"<p><p>Deconstructive transformation of carbon-carbon double bonds (C=C) is a pivotal strategy in synthetic chemistry and drug discovery. Despite the substantial advances in olefin metathesis and ozonolysis for natural product synthesis through C=C double-bond cleavage, the catalytic remodeling of complex molecules through C=C double-bond deconstruction has been underdeveloped. We report a heterogeneous copper-catalyzed C=C double-bond cleavage, which enables the remodeling of complex molecules by converting the carbons on either side of the C=C double bond to carbonyl and cyano groups, respectively. In particular, this method provides an efficient protocol to conveniently transform terpenoids, glycals, steroids, and bioactive molecules to privileged scaffolds with underexplored chemical space.</p>","PeriodicalId":21678,"journal":{"name":"Science","volume":"387 6738","pages":"1083-1090"},"PeriodicalIF":44.7000,"publicationDate":"2025-03-07","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Science","FirstCategoryId":"103","ListUrlMain":"https://doi.org/10.1126/science.adq8918","RegionNum":1,"RegionCategory":"综合性期刊","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2025/3/6 0:00:00","PubModel":"Epub","JCR":"Q1","JCRName":"MULTIDISCIPLINARY SCIENCES","Score":null,"Total":0}
引用次数: 0
Abstract
Deconstructive transformation of carbon-carbon double bonds (C=C) is a pivotal strategy in synthetic chemistry and drug discovery. Despite the substantial advances in olefin metathesis and ozonolysis for natural product synthesis through C=C double-bond cleavage, the catalytic remodeling of complex molecules through C=C double-bond deconstruction has been underdeveloped. We report a heterogeneous copper-catalyzed C=C double-bond cleavage, which enables the remodeling of complex molecules by converting the carbons on either side of the C=C double bond to carbonyl and cyano groups, respectively. In particular, this method provides an efficient protocol to conveniently transform terpenoids, glycals, steroids, and bioactive molecules to privileged scaffolds with underexplored chemical space.
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