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Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine

Journal Article


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Abstract


  • The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine is described. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide. Attempts to prepare the C-3a–C-11 ether moiety of this alkaloid through a photochemically induced oxidative cyclization method were unsuccessful because of the cleavage of the A-ring.

UOW Authors


  •   Dau, Xuan Duc (external author)
  •   Willis, Anthony C. (external author)
  •   Pyne, Stephen

Publication Date


  • 2015

Citation


  • Dau, X., Willis, A. C. & Pyne, S. G. (2015). Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine. European Journal of Organic Chemistry, 2015 (35), 7682-7694.

Scopus Eid


  • 2-s2.0-84948154868

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4393&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3370

Has Global Citation Frequency


Number Of Pages


  • 12

Start Page


  • 7682

End Page


  • 7694

Volume


  • 2015

Issue


  • 35

Place Of Publication


  • Germany

Abstract


  • The diastereoselective synthesis of the A-B-C tricyclic ring structure of the Stemona alkaloid stemocurtisine is described. This tricyclic precursor to the natural product was obtained in 19 steps from a known vinyl iodide. Attempts to prepare the C-3a–C-11 ether moiety of this alkaloid through a photochemically induced oxidative cyclization method were unsuccessful because of the cleavage of the A-ring.

UOW Authors


  •   Dau, Xuan Duc (external author)
  •   Willis, Anthony C. (external author)
  •   Pyne, Stephen

Publication Date


  • 2015

Citation


  • Dau, X., Willis, A. C. & Pyne, S. G. (2015). Diastereoselective synthesis of the A-B-C tricyclic ring structure of stemocurtisine. European Journal of Organic Chemistry, 2015 (35), 7682-7694.

Scopus Eid


  • 2-s2.0-84948154868

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=4393&context=smhpapers

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/3370

Has Global Citation Frequency


Number Of Pages


  • 12

Start Page


  • 7682

End Page


  • 7694

Volume


  • 2015

Issue


  • 35

Place Of Publication


  • Germany