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Synthesis of Complex and Diverse Compounds through Ring Distortion of Abietic Acid

Authors

  • Dr. Ryan J. Rafferty,

    1. Department of Chemistry, University of Illinois at Urbana-Champaign, 261 RAL, Box 36-5, 600 S. Mathews, Urbana, IL 61801 (USA)
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  • Robert W. Hicklin,

    1. Department of Chemistry, University of Illinois at Urbana-Champaign, 261 RAL, Box 36-5, 600 S. Mathews, Urbana, IL 61801 (USA)
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  • Katherine A. Maloof,

    1. Department of Chemistry, University of Illinois at Urbana-Champaign, 261 RAL, Box 36-5, 600 S. Mathews, Urbana, IL 61801 (USA)
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  • Prof. Paul J. Hergenrother

    Corresponding author
    1. Department of Chemistry, University of Illinois at Urbana-Champaign, 261 RAL, Box 36-5, 600 S. Mathews, Urbana, IL 61801 (USA)
    • Department of Chemistry, University of Illinois at Urbana-Champaign, 261 RAL, Box 36-5, 600 S. Mathews, Urbana, IL 61801 (USA)

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  • We are grateful to the Office of Naval Research (N00014-09-1-0249) and the University of Illinois at Urbana-Champaign for support of this work. We thank Dr. Danielle Gray for X-ray analysis of compound AA8. R.J.R. dedicates to Professor Robert M. Williams on the occasion of his 60th birthday.

Abstract

Many compound screening collections are populated by members that possess a low degree of structural complexity. In an effort to generate compounds that are both complex and diverse, we have developed a strategy that uses natural products as a starting point for complex molecule synthesis. Herein we apply this complexity-to-diversity approach to abietic acid, an abundant natural product used commercially in paints, varnishes, and lacquers. From abietic acid we synthesize a collection of complex (as assessed by fraction of sp3-hybridized carbons and number of stereogenic centers) and diverse (as assessed by Tanimoto analysis) small molecules. The 84 compounds constructed herein, and those created through similar efforts, should find utility in a variety of biological screens.

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