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  • Chem Sci Trans., 2013, 2(4),  pp 1496-1502  

    DOI:10.7598/cst2013.631

    Research Article

    Synthesis of Spirocyclopente-Dione Anthracene Adduct, Precursor of the Cyclopentenone Prostagladins Via Ring-Closing Metathesis Reaction

  • GEDSIRIN EKSINITKUN, STEPHEN G. PYNE, WAYA PHUTDHAWONG and WEERACHAI PHUTDHAWONG
  • Department of Chemistry, Faculty of Science, Silpakorn University, Nakhon Pathom-73000, Thailand
    School of Chemistry, University of Wollongong, Wollongong, N.S.W-2522, Australia
    Department of Chemistry, Faculty of Liberal Arts and Science, Kasetsart University, Kampeang Sean Campus, Nakhon Pathom-73140, Thailand
  • Abstract

    A synthesis of the spirocyclopente-dione anthracene adduct, a precursor of the cyclopentenone prostaglandins has been reported. The synthesis involved a Diels-Alder reaction of anthracene and dimethyl fumarate to afford 3 followed by reduction, oxidation and esterification reactions to provide methyl ester anthracene adduct 8, which further converted to the the allylic alcohol (12). Then, Ring-Closing Metathesis (RCM) reaction afforded the cyclopentenol anthracene adduct, which after oxidation provided the spirocyclopente-dione anthracene adduct in good yields.

    Keywords

    Cross-conjugated, Dienone, Ring closing metathesis, Cyclopentenones

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