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Synthesis of spirocyclopente-dione anthracene adduct, precursor of the cyclopentenone prostagladins via ring-closing metathesis reaction

Journal Article


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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.

UOW Authors


  •   Eksinitkun, Gedsirin (external author)
  •   Pyne, Stephen
  •   Phutdhawong, Waya S. (external author)
  •   Phutdhawong, Weerachai (external author)

Publication Date


  • 2013

Citation


  • Eksinitkun, G., Pyne, S. G., Phutdhawong, W. S. & Phutdhawong, W. (2013). Synthesis of spirocyclopente-dione anthracene adduct, precursor of the cyclopentenone prostagladins via ring-closing metathesis reaction. Chemical Science Transactions, 2 (4), 1496-1502.

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2647&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/1629

Number Of Pages


  • 6

Start Page


  • 1496

End Page


  • 1502

Volume


  • 2

Issue


  • 4

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.

UOW Authors


  •   Eksinitkun, Gedsirin (external author)
  •   Pyne, Stephen
  •   Phutdhawong, Waya S. (external author)
  •   Phutdhawong, Weerachai (external author)

Publication Date


  • 2013

Citation


  • Eksinitkun, G., Pyne, S. G., Phutdhawong, W. S. & Phutdhawong, W. (2013). Synthesis of spirocyclopente-dione anthracene adduct, precursor of the cyclopentenone prostagladins via ring-closing metathesis reaction. Chemical Science Transactions, 2 (4), 1496-1502.

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2647&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/1629

Number Of Pages


  • 6

Start Page


  • 1496

End Page


  • 1502

Volume


  • 2

Issue


  • 4