Total Synthesis of the Antitumor Antibiotic WF-3161

Authors

  • Prof. Dr. Ulrich Schmidt,

    Corresponding author
    1. Institut für Organische Chemie, Biochemie und Isotopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (FRG)
    • Institut Für Organische Chemie, Biochemie und Isotopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (FRG)
    Search for more papers by this author
  • Dipl.-Chem. Ulrich Beutler,

    1. Institut für Organische Chemie, Biochemie und Isotopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (FRG)
    Search for more papers by this author
  • Dr. Albrecht Lieberknecht

    1. Institut für Organische Chemie, Biochemie und Isotopenforschung der Universität, Pfaffenwaldring 55, D-7000 Stuttgart 80 (FRG)
    Search for more papers by this author

  • Amino Acids Peptides, Part 69; Cyclopeptides, Part 16. This work was supported by BASF AG, by the Fonds der Chemischen Industrie, and by Deutsche Forschungsgemeinschaft. –Parts 68 and 15: U. Schmidt, M. Kroner, H. Griesser, Tetrahedron Lett. 29 (1988) 4407.

Abstract

original image

The cyclopeptide WF-3161 (2) counts among the most effective cytostatics in vitro.—After stereoselective synthesis of the linear Z-tetrapeptide pentafluorophenyl ester 1, the ring is subsequently closed (in 74% yield) by catalytic hydrogenation. Conversion of the chloroketal into an epoxyketone completes the synthesis of the natural product.

Ancillary