A new synthesis of (-)-mesembrine employing sharpless AD reaction and new radical-initiated reaction

Takehiko Yoshimitsu, Kunio Ogasawara

Research output: Contribution to journalArticle

22 Citations (Scopus)

Abstract

Sharpless asymmetric dihydroxylation (AD reaction) of a σ-symmetric ethyl α,α-di[(E)-2-butenyl](3,4-dimethoxyphenyl)acetate allows an asymmetric construction of a quaternary carbon center by diastereoselective formation of the γ-lactone in moderate optical yields when double dihydroxylation occurs. The lactone generated is transformed into a Sceletium alkaloid (-)-mesembrine by discovery of the unprecedented radical-initiated cleavage reaction.

Original languageEnglish
Pages (from-to)135-139
Number of pages5
JournalHeterocycles
Volume42
Issue number1
Publication statusPublished - Dec 1 1996
Externally publishedYes

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ASJC Scopus subject areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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