Abstract
A facile, efficient, and scalable synthesis of optically pure coronafacic acid by resolution of racemic coronafacic acid obtained using an improved version of Watson's method has been developed. By optimizing the boron-mediated aldol reaction of Watson, we were able to prepare 2.1 g of racemic coronafacic acid. This was coupled with (S)-4-isopropyl-2-oxazolidinone to give a mixture of diastereomeric coronafacyl oxazolidinones, which were readily separable by silica-gel column chromatography to give 630 mg of optically pure (+)-coronafacic acid.
| Original language | English |
|---|---|
| Pages (from-to) | 423-430 |
| Number of pages | 8 |
| Journal | Chirality |
| Volume | 32 |
| Issue number | 4 |
| DOIs | |
| Publication status | Published - 2020 Apr 1 |
Keywords
- boron-mediated aldol reaction
- coronafacic acid
- coronatine
- jasmonates
- optical resolution
ASJC Scopus subject areas
- Analytical Chemistry
- Catalysis
- Pharmacology
- Drug Discovery
- Spectroscopy
- Organic Chemistry
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Cite this
Kato, N., Miyagawa, S., Nomoto, H., Nakayama, M., Iwashita, M., & Ueda, M. (2020). A scalable synthesis of (+)-coronafacic acid. Chirality, 32(4), 423-430. https://doi.org/10.1002/chir.23172