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

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JournalOrganic Letters
DatePublished - 17 Feb 2012
Issue number4
Volume14
Number of pages4
Pages (from-to)1122-1125
Original languageEnglish

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.

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