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

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

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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
Issue number4
Publication statusPublished - 17 Feb 2012

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