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Development of an Alkaloid–Pyrone Annulation: Synthesis of Pleiomaltinine

Authors

  • Robert E. Ziegler,

    1. Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215 (USA)
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  • Shin-Jowl Tan,

    1. Department of Chemistry, University of Malaysia, Kuala Lumpur 50603 (Malaysia)
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  • Prof. Dr. Toh-Seok Kam,

    1. Department of Chemistry, University of Malaysia, Kuala Lumpur 50603 (Malaysia)
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  • Prof. Dr. John A. Porco Jr.

    Corresponding author
    1. Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215 (USA)
    • Department of Chemistry, Center for Chemical Methodology and Library Development (CMLD-BU), Boston University, 590 Commonwealth Avenue, Boston, MA 02215 (USA)
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  • Financial support from the National Institutes of Health (R01 GM-073855) is gratefully acknowledged. We thank Prof. Stéphane Roche (Florida Atlantic University) and Prof. James Cook (University of Wisconsin-Milwaukee) for helpful discussions, and Dr. Jeffrey Bacon (Boston University) for X-ray crystal structure analysis.

Abstract

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Odd Couple: A method for the synthesis of alkaloid-pyrones using a novel pyrone annulation of β-carbolines and indoles with 3-siloxy-4-pyrones is reported. The approach has enabled synthesis of the unusual alkaloid-pyrone pleiomaltinine from the plant-derived indole-alkaloid pleiocarpamine (see Scheme; TBS= tert-butyldimethylsilyl).

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