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A concise and stereospecific synthesis of some cyclitols containing eight-membered rings: cyclooctane-1,2,3,4-tetraoles

Salamci, Emine


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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/23893</identifier>
  <creators>
    <creator>
      <creatorName>Salamci, Emine</creatorName>
      <givenName>Emine</givenName>
      <familyName>Salamci</familyName>
    </creator>
  </creators>
  <titles>
    <title>A Concise And Stereospecific Synthesis Of Some Cyclitols Containing Eight-Membered Rings: Cyclooctane-1,2,3,4-Tetraoles</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2010</publicationYear>
  <dates>
    <date dateType="Issued">2010-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/23893</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1016/j.tet.2010.04.052</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">A concise and efficient synthesis of cyclooctane-1,2,3,4-tetraoles, new polyhydroxylated eight-membered carbocycles, is described starting from cis,cis-1,3-cyclooctadiene. Cyclooctene endoperoxide obtained by photooxygenation of cis,cis-1,3-cyclooctadiene was the key compound in the synthesis. Reduction of the endoperoxide with zinc or thiourea followed by acetylation of the hydroxyl group and OsO4/NMO oxidation of the double bond gave (1R(S),2S(R),3R(S),4S(R))-cyclooctane-1,2,3,4-tetraol. Interestingly, epoxidation of cyclooctene-1,4-diol with m-CPBA also afforded trans-epoxy-diol 17. (1R(S),2R(S),3R(S),4S (R))-cyclooctane-1,2,3,4-tetraol was easily obtained by hydrolysis of epoxy-diol 17. (C) 2010 Elsevier Ltd. All rights reserved.</description>
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