Synthesis of monoterpene pyridine alkaloid aucubinine A

Xiao Bao Yang, Cheng Wen Hua, Hong Bin Zhai

Research output: Contribution to journalArticlepeer-review

Abstract

Aucubinine A, a monoterpene alkaloid isolated from the metabolites of aucubin in the presence of human intestinal bacteria, has been synthesized from 4-hydro-5-hydroxyl-3-methylidene-5H-cyclopentadieno[2,1-c]pyridine (6) in 30% overall yield. Hydroboration followed by oxidation in basic medium converted 6 to diastereomeric diols 7, which were subjected to selective benzylic oxidation to form aucubinine A.

Original languageEnglish
Pages (from-to)1429-1431
Number of pages3
JournalChinese Journal of Organic Chemistry
Volume24
Issue number11
StatePublished - Nov 2004
Externally publishedYes

Keywords

  • Aucubinine A
  • Cyclopentadieno[2,1-c]pyridine
  • Monoterpene alkaloid
  • Synthesis

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