A scalable synthesis of (+)-coronafacic acid

Nobuki Kato, Saki Miyagawa, Haruna Nomoto, Misuzu Nakayama, Makoto Iwashita, Minoru Ueda

Research output: Contribution to journalArticle

1 Citation (Scopus)

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 languageEnglish
Pages (from-to)423-430
Number of pages8
JournalChirality
Volume32
Issue number4
DOIs
Publication statusPublished - 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