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Stereoselective synthesis of α-methylenecyclopentenones via a Diels-Alder/retro-Diels-Alder protocol

Journal Article


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Abstract


  • A new procedure for the stereoselective synthesis of cross-conjugated dienones is reported. This method makes use of the Diels–Alder adduct of anthracene and dimethyl fumarate, a precursor to a spirocyclopent-2-enone anthracene adduct as the key intermediate. The addition of propyllithium or octyllithium to the key intermediate followed by a retro-Diels–Alder reaction furnished α-methylenecyclopentenones bearing a γ-propyl or γ-octyl side chain, respectively, in moderate yields and as single geometric isomers.

UOW Authors


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

Publication Date


  • 2013

Citation


  • Phutdhawong, W., Eksinitkun, G., Pyne, S. G., Willis, A. C. & Phutdhawong, W. S. (2013). Stereoselective synthesis of α-methylenecyclopentenones via a Diels-Alder/retro-Diels-Alder protocol. Tetrahedron, 69 (44), 9270-9276.

Scopus Eid


  • 2-s2.0-84884416286

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2260&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/1242

Number Of Pages


  • 6

Start Page


  • 9270

End Page


  • 9276

Volume


  • 69

Issue


  • 44

Abstract


  • A new procedure for the stereoselective synthesis of cross-conjugated dienones is reported. This method makes use of the Diels–Alder adduct of anthracene and dimethyl fumarate, a precursor to a spirocyclopent-2-enone anthracene adduct as the key intermediate. The addition of propyllithium or octyllithium to the key intermediate followed by a retro-Diels–Alder reaction furnished α-methylenecyclopentenones bearing a γ-propyl or γ-octyl side chain, respectively, in moderate yields and as single geometric isomers.

UOW Authors


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

Publication Date


  • 2013

Citation


  • Phutdhawong, W., Eksinitkun, G., Pyne, S. G., Willis, A. C. & Phutdhawong, W. S. (2013). Stereoselective synthesis of α-methylenecyclopentenones via a Diels-Alder/retro-Diels-Alder protocol. Tetrahedron, 69 (44), 9270-9276.

Scopus Eid


  • 2-s2.0-84884416286

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2260&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/1242

Number Of Pages


  • 6

Start Page


  • 9270

End Page


  • 9276

Volume


  • 69

Issue


  • 44