Total Synthesis of an Oxepine Natural Product, (±)-Janoxepin
- 30 January 2012
- journal article
- research article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 14 (4) , 1122-1125
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.Keywords
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