A scalable synthesis of (+)-coronafacic acid
Nobuki Kato1, Saki Miyagawa2, Haruna Nomoto1
1Department of Chemistry, Graduate School of Science, Tohoku University, Sendai, Japan.
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.
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