Total synthesis of the novel immunosuppressant sanglifehrin A

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

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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

All Science Journal Classification (ASJC) codes

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

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