Synthesis of demethylated nidulol via an intramolecular Michael reaction

Nat Prod Res. 2010 Aug;24(13):1274-81. doi: 10.1080/14786410903458265.

Abstract

An expeditious synthesis of 5,7-dihydroxy-6-methylphthalide from open-chain precursors is described. The key intermediates, synthons 3 and 4, were readily obtained from accessible materials and were further transformed to a common precursor, a five-membered lactone derivative, via an intramolecular Michael addition. Lactone 2 was aromatised to the phthalide system under basic conditions. The process thus constitutes a formal synthesis of the phthalide framework.

MeSH terms

  • Benzofurans / chemical synthesis*
  • Benzofurans / chemistry
  • Lactones / chemistry
  • Molecular Structure
  • Phthalic Anhydrides / chemical synthesis*
  • Spectrophotometry, Infrared

Substances

  • Benzofurans
  • Lactones
  • Phthalic Anhydrides
  • phthalide