{"title":"Synthetic Study on Bicyclic Pyranonaphthoquinone Natural Products: Construction of the Dioxabicyclo[3.3.1]nonene Motif","authors":"Yoshio Ando, Sota Ajima, Ken Ohmori","doi":"10.1002/ceur.202500086","DOIUrl":null,"url":null,"abstract":"<p>A concise method for the construction of dioxabicyclo[3.3.1]nonene framework has been developed. This structural motif has recently been identified in hybrid-type pyranonaphthoquinone-class natural products. The reaction proceeds in a stereoselective manner under mild conditions. In conjunction with this study, the scalable total syntheses of nanaomycins A and D have been achieved. Based on extensive screening of reaction conditions and nucleophiles, a plausible reaction mechanism is proposed.</p>","PeriodicalId":100234,"journal":{"name":"ChemistryEurope","volume":"3 4","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2025-05-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://onlinelibrary.wiley.com/doi/epdf/10.1002/ceur.202500086","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"ChemistryEurope","FirstCategoryId":"1085","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/ceur.202500086","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0
Abstract
A concise method for the construction of dioxabicyclo[3.3.1]nonene framework has been developed. This structural motif has recently been identified in hybrid-type pyranonaphthoquinone-class natural products. The reaction proceeds in a stereoselective manner under mild conditions. In conjunction with this study, the scalable total syntheses of nanaomycins A and D have been achieved. Based on extensive screening of reaction conditions and nucleophiles, a plausible reaction mechanism is proposed.
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