A new asymmetric synthesis of (R)-3-methylpyrrolidine alkaloids starting from (S)-malic acid

Xiao Zheng, Pei Qiang Huang*, Yuan Ping Ruan, Albert W M LEE, Wing Hong CHAN

*Corresponding author for this work

Research output: Contribution to journalJournal articlepeer-review

4 Citations (Scopus)

Abstract

Diastereoselective methylation of dimethyl (S)-malate (8) followed by two three-step reductive dehydroxylation procedures afforded dimethyl (R)-2-methylsuccinate (16) in 80.2% and 84.7% ee respectively, the later was further transformed into the natural enantiomers of ant venom alkaloids (R)-leptothoracine (1) and (R)-3-methyl-N-(2-phenylethyl)pyrrolidine (2) and (3R, 2'S)-3-methyl-N-(2-methylbutyl)pyrrolidine (3).

Original languageEnglish
Pages (from-to)1505-1518
Number of pages14
JournalHeterocycles
Volume55
Issue number8
DOIs
Publication statusPublished - 1 Aug 2001

Scopus Subject Areas

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

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