A scalable synthesis of (+)-coronafacic acid
Nobuki Kato1, Saki Miyagawa2, Haruna Nomoto1
1Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, Japan.
Chirality
|January 31, 2020
Summary
A new method efficiently synthesizes optically pure coronafacic acid. This scalable process improves upon Watson
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Chiral Synthesis
Background:
- Coronafacic acid is a key intermediate in synthesizing biologically active molecules.
- Previous synthesis methods for coronafacic acid were not scalable or efficient.
- Resolution of racemic mixtures is a common strategy for obtaining enantiomerically pure compounds.
Purpose of the Study:
- To develop a facile, efficient, and scalable synthesis of optically pure coronafacic acid.
- To optimize Watson's method for preparing racemic coronafacic acid.
- To establish a reliable method for resolving racemic coronafacic acid into its enantiomers.
Main Methods:
- Optimization of Watson's boron-mediated aldol reaction.
- Coupling of racemic coronafacic acid with (S)-4-isopropyl-2-oxazolidinone.
- Separation of diastereomeric oxazolidinones using silica-gel column chromatography.
Main Results:
- Successfully prepared 2.1 g of racemic coronafacic acid.
- Obtained a mixture of diastereomeric coronafacyl oxazolidinones.
- Isolated 630 mg of optically pure (+)-coronafacic acid with high purity.
Conclusions:
- The developed method provides a facile, efficient, and scalable route to optically pure coronafacic acid.
- This optimized synthesis and resolution technique offers a practical approach for obtaining enantiomerically pure coronafacic acid.
- The findings contribute to the advancement of chiral synthesis methodologies.
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