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


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.

DOI: 10.1021/ol300039x

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@article{Doveston2012TotalSO, title={Total synthesis of an oxepine natural product, (±)-janoxepin.}, author={Richard G Doveston and Ren{\'e} R. E. Steendam and Stuart O Jones and Richard J. Taylor}, journal={Organic letters}, year={2012}, volume={14 4}, pages={1122-5} }