Polycyclic ethers and an unexpected dearomatisation reaction during studies towards the bioactive alkaloid, perophoramidine

Craig A. Johnston, Ross P. Wilkie, Helmut Krauss, Andrew R. Neal, Alexandra M. Z. Slawin, Tomas Lebl, Nicholas J. Westwood

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)
8 Downloads (Pure)

Abstract

The bioactive alkaloid natural product perophoramidine and the related family of compounds known as the communesins have inspired the synthesis community for more than a decade. Many of the elegant approaches have required the synthesis of complex intermediates that have not always reacted in the expected manner. In this study we describe a series of cyclic ether-containing precursors that were prepared during our synthetic studies towards these natural products. Attempts to open the cyclic ether ring and trap the resulting stabilised carbocation with a carbon nucleophile ultimately led to the preparation of a diallyl-substituted all carbon quaternary centre. Subsequent attempts to differentiate between the two allyl groups resulted in a relatively clean transformation to an unexpected compound. Extensive structural characterisation, including small molecule X-ray crystallography, showed that a dearomatisation reaction had occurred.
Original languageEnglish
Pages (from-to)3339-3347
JournalTetrahedron
Volume74
Issue number26
Early online date28 Apr 2018
DOIs
Publication statusPublished - 28 Jun 2018

Keywords

  • Natural product
  • Ring opening reaction
  • Cyclic ether
  • Dearomatisation

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