Synthesis of complex and diverse compounds through ring distortion of abietic acid

Ryan J. Rafferty, Robert W. Hicklin, Katherine A. Maloof, Paul J. Hergenrother

Research output: Contribution to journalArticle

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 sp 3-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. Abietic acid was used as the starting point for the synthesis of 84 complex and diverse small molecules. Their complexity was assessed by the fraction of sp3-hybridized carbon atoms and the number of stereogenic centers, and their diversity was evaluated by Tanimoto analysis. The 84 compounds constructed herein, and those created through similar efforts, should find utility in a variety of biological screens.

Original languageEnglish (US)
Pages (from-to)220-224
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number1
DOIs
StatePublished - Jan 3 2014

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Biological Products
Molecules
Acids
Carbon
Lacquers
Varnish
Paint
Screening
Atoms
abietic acid

Keywords

  • abietic acid
  • high-throughput screening
  • molecular diversity
  • natural products
  • ring distortion

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

Cite this

Synthesis of complex and diverse compounds through ring distortion of abietic acid. / Rafferty, Ryan J.; Hicklin, Robert W.; Maloof, Katherine A.; Hergenrother, Paul J.

In: Angewandte Chemie - International Edition, Vol. 53, No. 1, 03.01.2014, p. 220-224.

Research output: Contribution to journalArticle

Rafferty, Ryan J. ; Hicklin, Robert W. ; Maloof, Katherine A. ; Hergenrother, Paul J. / Synthesis of complex and diverse compounds through ring distortion of abietic acid. In: Angewandte Chemie - International Edition. 2014 ; Vol. 53, No. 1. pp. 220-224.
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