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

X. Zheng, P. Q. Huang*, Y. P. Ruan, Albert W M LEE, Wing Hong CHAN

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Diastereoselective methylation of dimethyl (S)-malate 7, followed by two, three-step reductive de-hydroxylation procedures afforded dimethyl (R)-2-methylsuccinate 11 in 80.2% e.e. and 84.7% e.e., respectively. The latter compound was further transformed into the natural enantiomers of the ant venom alkaloids (R)-leptothoracine 1 and (R)-3-methyl-N-(2-phenylethyl)-pyrrolidine 2.

Original languageEnglish
Pages (from-to)53-56
Number of pages4
JournalNatural Product Letters
Volume16
Issue number1
DOIs
Publication statusPublished - 2002

Scopus Subject Areas

  • Molecular Medicine

User-Defined Keywords

  • Alkaloids
  • Asymmetric synthesis
  • Malic acid
  • Pyrrolidines

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