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Development of on-DNA Formation of Benzofuran for DNA-Encoded Library Synthesis.

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A new method synthesizes benzofurans on DNA using aldehydes. This powerful approach enables DNA-encoded library synthesis of diverse, medicinally important benzofuran scaffolds.

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Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Synthetic Chemistry

Background:

  • Benzofuran scaffolds are prevalent in pharmaceuticals.
  • Efficient synthesis of diverse benzofuran libraries is crucial for drug discovery.
  • DNA-encoded library (DEL) technology offers a powerful platform for screening large chemical spaces.

Purpose of the Study:

  • To develop a novel and efficient method for the on-DNA synthesis of benzofuran scaffolds.
  • To leverage a unique cascade reaction for constructing diverse benzofuran-based libraries.
  • To expand the utility of DNA-encoded library synthesis for accessing pharmaceutically relevant compounds.

Main Methods:

  • A novel homologation-heterocyclization cascade reaction was designed.
  • The methodology utilizes Seyferth-Gilbert homologation followed by in situ Sonogashira coupling and intramolecular cyclization.
  • The reaction sequence was optimized for one-pot, two-step execution on a DNA support.

Main Results:

  • Successful on-DNA synthesis of benzofurans from readily available aldehydes was achieved.
  • The developed cascade reaction demonstrated high yields and broad substrate scope.
  • A diverse array of pharmaceutically relevant benzofuran scaffolds was generated via DNA-encoded library synthesis.

Conclusions:

  • The novel homologation-heterocyclization cascade provides a powerful and unique pathway for DEL synthesis.
  • This methodology significantly expands the accessible chemical space for benzofuran-based drug discovery.
  • The developed on-DNA synthesis approach offers an efficient route to medicinally important scaffolds.