{"title":"Synthesis of functional allyl-α-tetrahydropyrones from cyrene","authors":"","doi":"10.1016/j.mencom.2024.06.016","DOIUrl":null,"url":null,"abstract":"<div><p>Addition of allylzinc to cyrene affords diastereomeric 4-allyl-6,8-dioxabicyclo[3.2.1]octan-4-ols. Opening of their 1,6-anhydro bridge with Ac<sub>2</sub>O followed by selective deacetylation of the resulting tertiary and acetal acetates yields diastereomeric 2-acetoxymethyl-5-allyl-tetrahydro- pyran-5,6-diols whose oxidation by the action of DMSO–Ac<sub>2</sub>O system is accompanied by etherification of tertiary hydroxy groups leading to methylthiomethoxy pyrone derivatives. The opening of 1,6-anhydro bridge in 4-allyl-6,8-dioxabicyclo[3.2.1]octan-4-ols with MeOH–HCl followed by oxidation with PCC gives individual (4<em>S</em>,6<em>S</em>)- 1-allyl-6-methoxy-2,5-dioxabicyclo[2.2.2]octan-3-one.</p></div>","PeriodicalId":18542,"journal":{"name":"Mendeleev Communications","volume":null,"pages":null},"PeriodicalIF":1.8000,"publicationDate":"2024-07-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Mendeleev Communications","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0959943624001937","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0
Abstract
Addition of allylzinc to cyrene affords diastereomeric 4-allyl-6,8-dioxabicyclo[3.2.1]octan-4-ols. Opening of their 1,6-anhydro bridge with Ac2O followed by selective deacetylation of the resulting tertiary and acetal acetates yields diastereomeric 2-acetoxymethyl-5-allyl-tetrahydro- pyran-5,6-diols whose oxidation by the action of DMSO–Ac2O system is accompanied by etherification of tertiary hydroxy groups leading to methylthiomethoxy pyrone derivatives. The opening of 1,6-anhydro bridge in 4-allyl-6,8-dioxabicyclo[3.2.1]octan-4-ols with MeOH–HCl followed by oxidation with PCC gives individual (4S,6S)- 1-allyl-6-methoxy-2,5-dioxabicyclo[2.2.2]octan-3-one.
期刊介绍：
Mendeleev Communications is the journal of the Russian Academy of Sciences, launched jointly by the Academy of Sciences of the USSR and the Royal Society of Chemistry (United Kingdom) in 1991. Starting from 1st January 2007, Elsevier is the new publishing partner of Mendeleev Communications.
Mendeleev Communications publishes short communications in chemistry. The journal primarily features papers from the Russian Federation and the other states of the former USSR. However, it also includes papers by authors from other parts of the world. Mendeleev Communications is not a translated journal, but instead is published directly in English. The International Editorial Board is composed of eminent scientists who provide advice on refereeing policy.
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