Jonathan Trevorrow , Nhlanhla Sibanda , Anne O'Kearney‐McMullan , Lucie Miller Potucka , Adrian P. Dobbs
{"title":"Oxidative Photochemical Cyclisations to Access Spiroketals","authors":"Jonathan Trevorrow , Nhlanhla Sibanda , Anne O'Kearney‐McMullan , Lucie Miller Potucka , Adrian P. Dobbs","doi":"10.1002/adsc.202400393","DOIUrl":null,"url":null,"abstract":"<div><div>The spiroketal moiety is an important substructure within many biological natural products. One method to access them is <em>via</em> the oxidative cyclisation of a pendant hydroxyl group on to a pre‐formed pyran. However applications of this methodology have been severely limited by requiring the use of toxic oxidants, such as lead (IV) tetraacetate or mercuric oxide. Herein we report a high yielding photochemical route to prepare complex spiroketals using an oxidative photochemical approach employing iodine monochloride and sodium acetate and demonstrate the methodology to the synthesis of a number of insect pheromones.</div></div>","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"366 22","pages":"Pages 4694-4701"},"PeriodicalIF":4.4000,"publicationDate":"2024-11-19","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/adsc.202400393","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S161541502400709X","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
The spiroketal moiety is an important substructure within many biological natural products. One method to access them is via the oxidative cyclisation of a pendant hydroxyl group on to a pre‐formed pyran. However applications of this methodology have been severely limited by requiring the use of toxic oxidants, such as lead (IV) tetraacetate or mercuric oxide. Herein we report a high yielding photochemical route to prepare complex spiroketals using an oxidative photochemical approach employing iodine monochloride and sodium acetate and demonstrate the methodology to the synthesis of a number of insect pheromones.
期刊介绍：
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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