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Asymmetric Total Synthesis of the Epoxykinamycin FL-120 B′

Authors

  • Stephen S. Scully,

    1. Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215 (USA)
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  • Prof. Dr. John A. Porco Jr.

    Corresponding author
    1. Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215 (USA)
    • Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215 (USA)
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  • This work was presented in part at the 237th American Chemical Society National Meeting, Boston, MA, August 19-23, 2007; ORGN abstract 667. Financial support from the National Institutes of Health (RO1 CA137270) is gratefully acknowledged. We thank Arthur Su (Boston University) for helpful discussions, Dr. Paul Ralifo (Boston University) for NMR assistance, Dr. Norman Lee (Boston University) for HPLC assistance, and Dr. Jenn-jong Young (Institute of Preventive Medicine (Taiwan, ROC)) for generously providing a sample of FL-120B.

Abstract

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Heiße Sache: Eine Route zu Diazobenzofluorenen mit Epoxidgruppen als potenzielle Monomere für die dimeren Lomaiviticine wird vorgestellt. Schlüsselschritte beim Aufbau des FL-120B′-Kerns in der Synthese der Titelverbindung sind eine Sharpless-Epoxidierung, eine Stille-Kupplung und eine intramolekulare Friedel-Crafts-Acylierung von atropisomeren Carbonsäuren unter Erhitzen.

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