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A planning strategy for diversity-oriented synthesis.

Martin D Burke1, Stuart L Schreiber

  • 1Department of Chemistry and Chemical Biology, Howard Hughes Medical Institute, ICCB, Harvard University, 12 Oxford Street, Cambridge, MA 02138, USA.

Angewandte Chemie (International Ed. in English)
|December 25, 2003
PubMed
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Diversity-oriented synthesis (DOS) broadly populates chemical space with diverse small molecules. This approach enables efficient synthesis and appendage attachment for drug discovery, utilizing forward-synthetic analysis.

Area of Science:

  • Organic Chemistry
  • Medicinal Chemistry
  • Chemical Biology

Background:

  • Target-oriented synthesis (TOS) and medicinal/combinatorial chemistry focus on precise or dense chemical space exploration.
  • Diversity-oriented synthesis (DOS) broadly populates chemical space with structurally diverse small molecules.

Purpose of the Study:

  • To develop efficient (3-5 step) synthetic pathways for diverse small molecules.
  • To enable site- and stereoselective appendage attachment for post-screening maturation.
  • To ensure diverse positioning of appendages on molecule surfaces.

Main Methods:

  • Development of efficient synthetic pathways for skeletal and stereochemical diversity.
  • Utilizing parallel logic to develop forward-synthetic analysis.

Related Experiment Videos

  • Establishing defined coordinates in chemical space for synthesized molecules.

    • Main Results:

    • Creation of diverse small-molecule collections with skeletal and stereochemical variety.
    • Identification of compounds amenable to site- and stereoselective appendage attachment.
    • Development of a complementary forward-synthetic analysis procedure.

    Conclusions:

    • DOS offers a complementary approach to TOS and medicinal chemistry for chemical space exploration.
    • Forward-synthetic analysis facilitates synthetic planning, communication, and teaching in DOS.
    • DOS generates diverse molecular scaffolds crucial for drug discovery and development.