Intramolecular Michael reaction in diastereoselective synthesis of dl-Griseofulvin

Yasuo Takeuchi, I. Watanabe, H. Tomozane, K. Hashigaki, M. Yamato

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Abstract

The diastereoselective cyclization of 2a to 5a, which was employed in our novel synthesis of dl-griseofulvin (7a), was studied in detail. It was found that the use of the metallic bases resulted in excellent diastereoselectively, whereas organic bases are ineffective for diastereoselective cyclization. Consequently, diastereoselective cyclization of 2 to 5 was proposed to proceed through the intramolecular Michael reaction under chelation control.

Original languageEnglish
Pages (from-to)3048-3050
Number of pages3
JournalChemical and Pharmaceutical Bulletin
Volume39
Issue number11
Publication statusPublished - 1991

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ASJC Scopus subject areas

  • Chemistry(all)
  • Organic Chemistry
  • Drug Discovery
  • Pharmacology

Cite this

Takeuchi, Y., Watanabe, I., Tomozane, H., Hashigaki, K., & Yamato, M. (1991). Intramolecular Michael reaction in diastereoselective synthesis of dl-Griseofulvin. Chemical and Pharmaceutical Bulletin, 39(11), 3048-3050.