title: Total synthesis of an oxepine natural product, (±)-janoxepin.
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.
authors.affiliation: Department of Chemistry, University of York, Heslington, York YO10 5DD, UK.
authors.forename: Richard G
authors.initials: RG
authors.lastname: Doveston
authors.forename: René
authors.initials: R
authors.lastname: Steendam
authors.forename: Stuart
authors.initials: S
authors.lastname: Jones
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor
mesh_terms: D001230:Aspergillus / Q000737:chemistry*; D001688:Biological Products / Q000138:chemical synthesis*; D008958:Models, Molecular; D015394:Molecular Structure; D010879:Piperazines / Q000737:chemistry*; D011744:Pyrimidinones / Q000138:chemical synthesis / Q000737:chemistry*
chemical_list: D001688:Biological Products; D010879:Piperazines; D011744:Pyrimidinones; C572088:janoxepin