Total synthesis of an oxepine natural product, (±)-janoxepin

Richard G. Doveston, René Steendam, Stuart Jones, Richard J K Taylor

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27 Citations (Scopus)

Abstract

The total synthesis of (±)-janoxepin, a novel antiplasmodial d-leucine derived oxepine-pyrimidinone-ketopiperazine isolated from the fungus Aspergillus janus, is described. The cornerstones of the synthetic route are pyrimidinone preparation, ring-closing metathesis, aldol introduction of the enamide, and dihydro-oxepine elaboration. This synthetic route proved very efficient for the formation of a number of janoxepin analogues, including dihydro-janoxepin and tetrahydro-janoxepin.

Original languageEnglish
Pages (from-to)1122-1125
Number of pages4
JournalOrganic Letters
Volume14
Issue number4
Early online date30 Jan 2012
DOIs
Publication statusPublished - 17 Feb 2012

Keywords

  • oxepine
  • janoxepin
  • Aspergillus janus

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    Doveston, R. G., Steendam, R., Jones, S., & Taylor, R. J. K. (2012). Total synthesis of an oxepine natural product, (±)-janoxepin. Organic Letters, 14(4), 1122-1125. https://doi.org/10.1021/ol300039x