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December 3, 2025The Journal of Organic Chemistry

Desymmetrization of meso -Anhydride Enabled Enantioselective Synthesis of (−)-7-(Bromomethylene)-3-amidobicyclo2.2.1heptane-2-carboxamide, a Scaffold for Divergent Drug Discovery Synthesis

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Authors

JLJianqing LiNanjing University of Chinese MedicineSKSubramaniam KrishnananthanBristol-Myers Squibb (Germany)DSDaniel SmithBristol-Myers Squibb (Germany)

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Overview

Enantioselective synthesis achieves >99% ee in scaffold for drug discovery, suggesting new pathways in medicinal chemistry.

Key Points

  • Synthesis yielded a drug scaffold with greater than 99% enantiomeric excess, indicating high precision in drug design.
  • Key steps included Diels-Alder reaction with maleic anhydride and quinidine-mediated desymmetrization, achieving >93% ee for hydroxyl groups.
  • Utilization of chiral resolution together with Curtius rearrangement and Swern oxidation enabled efficient compound formation.
  • This method highlights the potential for creating complex drug structures via advanced synthetic techniques.

Cite This Study

Li et al. (2025) studied this question.

synapsesocial.com/papers/694025842d562116f28fe6ebhttps://doi.org/10.1021/acs.joc.5c02021
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