Total Synthesis and Stereochemical Revision of Phacelocarpus 2-Pyrone A

Thomas O. Ronson, Michael J. Burns, Martin H H Voelkel, Kieren J. Evans, Jason M. Lynam, Richard J K Taylor*, Ian J S Fairlamb

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review


The first total synthesis of phacelocarpus 2-pyrone A is reported. The original natural compound was tentatively assigned (by NMR spectroscopy) as containing two cis-alkenes and a trans-vinyl ether connected to a 2-pyrone ring motif. Our computational predictions indicated that a cis-vinyl ether motif was equally feasible. Attempts to prepare the trans-vinyl ether were met with no success. The all cis-target compound was synthesised in nine steps, employing key regio- and stereoselective reactions including AuI-catalysed vinyl etherification, Wittig alkenylation and end-game Stille macrocyclisation. Analysis of the NMR data enabled identification and confirmation of the correct structure of phacelocarpus 2-pyrone A, containing a cis-vinyl ether. Our studies pave the way for future development of methodologies to these structurally distinct pyrone skipped-polyenyne natural products.

Original languageEnglish
Pages (from-to)18905-18909
Number of pages5
JournalChemistry : A European Journal
Issue number52
Publication statusPublished - 21 Dec 2015


  • dienes
  • macrocycles
  • natural products
  • palladium
  • total synthesis

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