title: Oxidative carbocation formation in macrocycles: synthesis of the neopeltolide macrocycle.
abstract: Macrocyclic oxocarbenium ions can be formed from macrolactones that contain benzylic or allylic ether groups through oxidative carbon-hydrogen-bond activation mediated by 2,3-dichloro-4,5-dicyanoquinone (DDQ). The applicability of this efficient reaction to complex-molecule synthesis was demonstrated by its use in a brief formal synthesis of neopeltolide (see retrosynthetic scheme) to form the tetrahydropyrone ring.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, PA 15260, USA.
authors.forename: Wangyang
authors.initials: W
authors.lastname: Tu
authors.forename: Paul E
authors.initials: PE
authors.lastname: Floreancig
mesh_terms: D003500:Cyclization; D018942:Macrolides / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction
chemical_list: D018942:Macrolides; C519136:neopeltolide