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Model support studies toward the total synthesis of the stemona alkaloid stemocurtisine

Journal Article


Abstract


  • Herein we report the results of a furan-based approach toward the synthesis of the Stemona alkaloid, stemocurtisine 1 via the linearly fused tricyclic intermediate 3, representing the key A,B,C-ring structural feature of the target molecule. A highly diastereoselective synthesis of compound 3 was achieved starting from 3-furfural 6, in a synthetic sequence that involved; (1) a rapid in situ conversion of an O-mesylate to the corresponding chloride with inversion of configuration from assistance of the neighbouring 3-furanyl group; (2) an intramolecular aza-Wittig reaction to prepare the azepine ring; and (3) a base promoted lactam ring forming step. While methods were established to oxidize the furan ring of 3 to the corresponding γ-hydroxy-α,β-unsaturated lactone we were unable to affect cyclization of the lactam ring hydroxyl group to the γ-position of the lactone to create the cyclic ether feature of the natural product. Model studies were also unsuccessful.

UOW Authors


  •   Shengule, Sudhir R. (external author)
  •   Willis, Anthony C. (external author)
  •   Pyne, Stephen

Publication Date


  • 2013

Citation


  • Shengule, S. R., Willis, A. C. & Pyne, S. G. (2013). Model support studies toward the total synthesis of the stemona alkaloid stemocurtisine. Tetrahedron, 69 (37), 8042-8050.

Scopus Eid


  • 2-s2.0-84880916382

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/1057

Has Global Citation Frequency


Number Of Pages


  • 8

Start Page


  • 8042

End Page


  • 8050

Volume


  • 69

Issue


  • 37

Place Of Publication


  • United Kingdom

Abstract


  • Herein we report the results of a furan-based approach toward the synthesis of the Stemona alkaloid, stemocurtisine 1 via the linearly fused tricyclic intermediate 3, representing the key A,B,C-ring structural feature of the target molecule. A highly diastereoselective synthesis of compound 3 was achieved starting from 3-furfural 6, in a synthetic sequence that involved; (1) a rapid in situ conversion of an O-mesylate to the corresponding chloride with inversion of configuration from assistance of the neighbouring 3-furanyl group; (2) an intramolecular aza-Wittig reaction to prepare the azepine ring; and (3) a base promoted lactam ring forming step. While methods were established to oxidize the furan ring of 3 to the corresponding γ-hydroxy-α,β-unsaturated lactone we were unable to affect cyclization of the lactam ring hydroxyl group to the γ-position of the lactone to create the cyclic ether feature of the natural product. Model studies were also unsuccessful.

UOW Authors


  •   Shengule, Sudhir R. (external author)
  •   Willis, Anthony C. (external author)
  •   Pyne, Stephen

Publication Date


  • 2013

Citation


  • Shengule, S. R., Willis, A. C. & Pyne, S. G. (2013). Model support studies toward the total synthesis of the stemona alkaloid stemocurtisine. Tetrahedron, 69 (37), 8042-8050.

Scopus Eid


  • 2-s2.0-84880916382

Ro Metadata Url


  • http://ro.uow.edu.au/smhpapers/1057

Has Global Citation Frequency


Number Of Pages


  • 8

Start Page


  • 8042

End Page


  • 8050

Volume


  • 69

Issue


  • 37

Place Of Publication


  • United Kingdom