Stereocontrolled syntheses of tetralone- and naphthyl-type lignans by a one-pot oxidative [3,3] rearrangement/friedel-crafts arylation

Jordan C.T. Reddel, Kelly E. Lutz, Abdallah B. Diagne, Regan J. Thomson*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

29 Scopus citations

Abstract

The development of a stereoselective one-pot oxidative [3,3] sigmatropic rearrangement/Friedel-Crafts arylation that provides enantioenriched benzhydryl compounds is reported. The utility of this new transformation is demonstrated by the concise synthesis of several tetralone- and naphthyl-type lignan natural products, many of which display anti-malarial activity.

Original languageEnglish (US)
Pages (from-to)1395-1398
Number of pages4
JournalAngewandte Chemie - International Edition
Volume53
Issue number5
DOIs
StatePublished - Jan 27 2014

Keywords

  • Cascade reactions
  • Hydrazones
  • Lignans
  • Natural product synthesis
  • Sigmatropic rearrangement

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)

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