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Structural revision of stemoburkilline from an E-alkene to a Z-alkene

Journal Article


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Abstract


  • Semisynthesis studies starting from (11Z)-1',2'-didehydrostemofoline (4) indicated that the known Stemona alkaloid stemoburkilline is the Z-isomer and not the E-isomer as initially reported. The semisynthesis involved conversion of (11Z)-1',2'-didehydrostemofoline (4) to 11(S),12(S)-dihydrostemofoline (3) followed by a stereoselective base-catalyzed ring-opening reaction to give (Z)-stemoburkilline (8). The same product was obtained using a similar synthetic protocol starting from isostemofoline (6) via a based-catalyzed ring-opening reaction of 11(S), 12(R)-dihydrostemofoline (1). A re-examination of the crude root extracts of Stemona burkillii Prain and further NOE studies established stemoburkilline as the Z-isomer (8).

UOW Authors


  •   Sastraruji, Kwankamol (external author)
  •   Pyne, Stephen
  •   Ung, Alison T. (external author)
  •   Mungkornasawakul, Pitchaya (external author)
  •   Lie, Wilford
  •   Jatisatienr, Araya (external author)

Publication Date


  • 2009

Citation


  • Sastraruji, K., Pyne, S. G., Ung, A. T., Mungkornasawakul, P., Lie, W. & Jatisatienr, A. (2009). Structural revision of stemoburkilline from an E-alkene to a Z-alkene. Journal of Natural Products, 72 (2), 316-318.

Scopus Eid


  • 2-s2.0-62649115548

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2203&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/1135

Number Of Pages


  • 2

Start Page


  • 316

End Page


  • 318

Volume


  • 72

Issue


  • 2

Abstract


  • Semisynthesis studies starting from (11Z)-1',2'-didehydrostemofoline (4) indicated that the known Stemona alkaloid stemoburkilline is the Z-isomer and not the E-isomer as initially reported. The semisynthesis involved conversion of (11Z)-1',2'-didehydrostemofoline (4) to 11(S),12(S)-dihydrostemofoline (3) followed by a stereoselective base-catalyzed ring-opening reaction to give (Z)-stemoburkilline (8). The same product was obtained using a similar synthetic protocol starting from isostemofoline (6) via a based-catalyzed ring-opening reaction of 11(S), 12(R)-dihydrostemofoline (1). A re-examination of the crude root extracts of Stemona burkillii Prain and further NOE studies established stemoburkilline as the Z-isomer (8).

UOW Authors


  •   Sastraruji, Kwankamol (external author)
  •   Pyne, Stephen
  •   Ung, Alison T. (external author)
  •   Mungkornasawakul, Pitchaya (external author)
  •   Lie, Wilford
  •   Jatisatienr, Araya (external author)

Publication Date


  • 2009

Citation


  • Sastraruji, K., Pyne, S. G., Ung, A. T., Mungkornasawakul, P., Lie, W. & Jatisatienr, A. (2009). Structural revision of stemoburkilline from an E-alkene to a Z-alkene. Journal of Natural Products, 72 (2), 316-318.

Scopus Eid


  • 2-s2.0-62649115548

Ro Full-text Url


  • http://ro.uow.edu.au/cgi/viewcontent.cgi?article=2203&context=scipapers

Ro Metadata Url


  • http://ro.uow.edu.au/scipapers/1135

Number Of Pages


  • 2

Start Page


  • 316

End Page


  • 318

Volume


  • 72

Issue


  • 2