title: The first synthesis of the ABC-ring system of 'upenamide.
abstract: The first synthetic route to the spirooxaquinolizidinone core (ABC core) of the macrocyclic marine alkaloid 'upenamide (1) has been developed. All five stereocenters were introduced with complete stereocontrol. The hydroxyl group at C-11 was introduced by a regio- and stereoselective SeO(2)-mediated allylic oxidation. The spirocyclic skeleton was formed by a stannous chloride induced deacetalization-bicyclization procedure. Further stereocenters were introduced by an enzymatic desymmetrization and by incorporation of an (S)-malic acid derived building block.
authors.affiliation: Department of Chemistry, University of York, York, YO10 5DD, U.K.
authors.forename: Jan Peter
authors.initials: JP
authors.lastname: Schmidt
authors.forename: Sandra
authors.initials: S
authors.lastname: Beltrán-Rodil
authors.forename: Rhona J
authors.initials: RJ
authors.lastname: Cox
authors.forename: Graeme D
authors.initials: GD
authors.lastname: McAllister
authors.forename: Mark
authors.initials: M
authors.lastname: Reid
authors.forename: Richard J K
authors.initials: RJ
authors.lastname: Taylor
mesh_terms: D009682:Magnetic Resonance Spectroscopy; D008958:Models, Molecular; D015394:Molecular Structure; D011807:Quinolizines / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D011807:Quinolizines; D013141:Spiro Compounds; C418125:upenamide