Total Synthesis of Cyanolide A in the Absence of Protecting Groups, Chiral Auxiliaries, or Premetalated Carbon Nucleophiles

Authors

  • Andrew R. Waldeck,

    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station—A5300, Austin, TX 78712-1167 (USA)
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  • Prof. Michael J. Krische

    Corresponding author
    1. University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station—A5300, Austin, TX 78712-1167 (USA)
    • University of Texas at Austin, Department of Chemistry and Biochemistry, 1 University Station—A5300, Austin, TX 78712-1167 (USA)===

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  • Acknowledgements are made to the Robert A. Welch Foundation (F-0038) and the NIH-NIGMS (RO1-GM093905) for partial financial support. Dr. Abbas Hassan and Dr. Anne-Marie Dechert-Schmitt are gratefully acknowledged for technical assistance.

Abstract

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Keine Schutzgruppen: Eine Synthese des C2-symmetrischen Makrodiolids Cyanolid A in sechs Stufen ausgehend von Neopentylglycol und Allylacetat beruht auf einer iridiumkatalysierten doppelten asymmetrischen Allylierung und einer Tandemreaktion aus Kreuzmetathese und Oxa-Michael-Cyclisierung zur Bildung des substituierten Pyranrings. Die Synthese gelang ohne Einsatz von Schutzgruppen, chiralen Auxiliaren und zuvor metallierten Kohlenstoffnucleophilen.

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