Total synthesis of the novel immunosuppressant sanglifehrin A

K. C. Nicolaou, F. Murphy, S. Barluenga, Takashi Ohshima, H. Wei, J. Xu, D. L.F. Gray, O. Baudoin

Research output: Contribution to journalArticle

79 Citations (Scopus)

Abstract

The total synthesis of the novel immunosuppressant sanglifehrin A (SFA, 1) is described. The approach is flexible, convergent, and stereoselective. The use of Paterson's aldol methodology was pivotal for the preparation of the novel, highly substituted spirolactam fragment of SFA. The 22-membered macrocyclic core of the molecule and the coupling of this fragment to the spirolactam moiety were successfully achieved using selective intra- and intermolecular Stille reactions, respectively. Carbodiimide-based protocols were employed for the synthesis of the tripeptide backbone.

Original languageEnglish
Pages (from-to)3830-3838
Number of pages9
JournalJournal of the American Chemical Society
Volume122
Issue number16
DOIs
Publication statusPublished - Apr 26 2000
Externally publishedYes

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Carbodiimides
Immunosuppressive Agents
Molecules
3-hydroxybutanal
sanglifehrin A

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Nicolaou, K. C., Murphy, F., Barluenga, S., Ohshima, T., Wei, H., Xu, J., ... Baudoin, O. (2000). Total synthesis of the novel immunosuppressant sanglifehrin A. Journal of the American Chemical Society, 122(16), 3830-3838. https://doi.org/10.1021/ja994285v

Total synthesis of the novel immunosuppressant sanglifehrin A. / Nicolaou, K. C.; Murphy, F.; Barluenga, S.; Ohshima, Takashi; Wei, H.; Xu, J.; Gray, D. L.F.; Baudoin, O.

In: Journal of the American Chemical Society, Vol. 122, No. 16, 26.04.2000, p. 3830-3838.

Research output: Contribution to journalArticle

Nicolaou, KC, Murphy, F, Barluenga, S, Ohshima, T, Wei, H, Xu, J, Gray, DLF & Baudoin, O 2000, 'Total synthesis of the novel immunosuppressant sanglifehrin A', Journal of the American Chemical Society, vol. 122, no. 16, pp. 3830-3838. https://doi.org/10.1021/ja994285v
Nicolaou, K. C. ; Murphy, F. ; Barluenga, S. ; Ohshima, Takashi ; Wei, H. ; Xu, J. ; Gray, D. L.F. ; Baudoin, O. / Total synthesis of the novel immunosuppressant sanglifehrin A. In: Journal of the American Chemical Society. 2000 ; Vol. 122, No. 16. pp. 3830-3838.
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