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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