Gas-phase domino cyclisation of phosphonium ylides leading to the total synthesis of Eustifoline D

R. Alan Aitken, Lorna Murray

Research output: Contribution to journalArticlepeer-review

4 Citations (Scopus)

Abstract

Six stabilised phosphonium ylides bearing ortho-benzylaminophenyl and cinnamoyl (or a heterocyclic analogue) groups have been prepared and upon flash vacuum pyrolysis at 800 °C were found to undergo cascade cyclization processes to give mainly 3-styrylquinolines but also in some cases ring-fused carbazoles and other fused-ring heterocyclic products. By starting with an appropriate ring-methylated precursor the natural product Eustifoline D was obtained in 19% yield in the pyrolysis in addition to the 3-(2-furylethenyl)quinoline (46%).
Original languageEnglish
Pages (from-to)4328-4332
Number of pages5
JournalTetrahedron Letters
Volume58
Issue number46
Early online date27 Sept 2017
DOIs
Publication statusPublished - 15 Nov 2017

Keywords

  • Cyclization
  • Gas-phase reaction
  • Phosphorus ylides
  • Fused-ring systems
  • Radical reaction

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