Synthesis of demethylated nidulol via an intramolecular Michael reaction

Rogelio Jiménez, Luís A. Maldonado, Héctor Salgado-Zamora

Research output: Contribution to journalArticlepeer-review

2 Scopus citations

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.

Original languageEnglish
Pages (from-to)1274-1281
Number of pages8
JournalNatural Product Research
Volume24
Issue number13
DOIs
StatePublished - Aug 2010

Keywords

  • intramolecular aromatisation
  • nidulol
  • phthalides

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