Intramolecular Michael Reaction in Diastereoselective Synthesis of dl-Griseofulvin

Yasuo Takeuchi, Ikuo Watanabe, Hideo Tomozane, Kuniko Hashigaki, Masatoshi Yamato

Research output: Contribution to journalArticle

1 Citation (Scopus)

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
DOIs
Publication statusPublished - Jan 1 1991

Keywords

  • chelation control
  • diastereoselective Michael reaction
  • dl-griseofulvin
  • reaction mechanism

ASJC Scopus subject areas

  • Chemistry(all)
  • Drug Discovery

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