A short stereoselective synthesis of racemic 2-epicalvine

Basem A. Moosa, Shaikh A. Ali

Research output: Contribution to journalArticlepeer-review

2 Scopus citations


The cycloaddition reaction of 6-pentyl-3,4,5,6-tetrahydropyridine 1-oxide with butyl vinyl ether was used as a key step in the short stereoselective racemic synthesis of ladybird beetle alkaloid, 2-epicalvine. The cycloadduct was subjected to quaternization with 2-bromoethanol, followed by ring opening and lactonization to afford the natural product in a one-pot reaction.

Original languageEnglish (US)
Pages (from-to)1191-1194
Number of pages4
JournalNatural Product Communications
Issue number8
StatePublished - 2010
Externally publishedYes


  • Epicalvine
  • Natural products
  • Nitrone cycloaddition
  • Piperidines
  • Stereoselective synthesis

ASJC Scopus subject areas

  • Drug Discovery
  • Pharmacology
  • Complementary and alternative medicine
  • Plant Science
  • Medicine(all)


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