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Related Experiment Videos

A three-component coupling approach to cyclopentanoids.

B M Trost1, A B Pinkerton

  • 1Department of Chemistry, Stanford University, Stanford, California 94305, USA. bmtrost@stanford.edu

The Journal of Organic Chemistry
|November 10, 2001
PubMed
Summary
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A novel synthetic route efficiently produces 2,3-disubstituted cyclopentenones. This method utilizes a two-step process starting with a Z-vinyl bromide, enabling the synthesis of valuable compounds like jasmone and pharmaceuticals.

Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Cyclopentenones are important structural motifs in natural products and pharmaceuticals.
  • Efficient and versatile synthetic methods for 2,3-disubstituted cyclopentenones are highly sought after.

Purpose of the Study:

  • To develop a new, efficient synthetic strategy for accessing 2,3-disubstituted cyclopentenones.
  • To demonstrate the broad applicability of this new method in synthesizing complex molecules.

Main Methods:

  • A ruthenium-catalyzed three-component coupling reaction to form Z-vinyl bromides.
  • A two-step protocol involving Barbier-type cyclization followed by oxidative rearrangement.

Main Results:

  • Successful synthesis of a range of 2,3-disubstituted cyclopentenones.

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  • Short syntheses of jasmone and dihydrojasmone were achieved.
  • Demonstrated utility in total syntheses of tetrahydrodicranenone B, rosaprostol, and a COX-2 inhibitor.

    • Conclusions:

    • The developed method provides a robust and versatile approach to 2,3-disubstituted cyclopentenones.
    • This strategy offers a valuable tool for the synthesis of biologically active compounds and natural products.