title: Photooxygenation of a microbial arene oxidation product and regioselective Kornblum-DeLaMare rearrangement: total synthesis of zeylenols and zeylenones.
abstract: We report the enantioselective total syntheses of zeylenol (+)-1, as well as its congeners (-)-7 and 16, and of 3-O-debenzoylzeylenone 28. To this end, a new variant of the Kornblum-DeLaMare rearrangement, which utilises neighbouring-group participation to impart regioselectivity, has been developed. The approach employs photooxygenation of building blocks derived from a microbial arene oxidation product.
authors.affiliation: Department of Chemistry, University of Bath, Claverton Down, Bath, BA2 7AY, United Kingdom.
authors.forename: Matthew J
authors.initials: MJ
authors.lastname: Palframan
authors.forename: Gabriele
authors.initials: G
authors.lastname: Kociok-Köhn
authors.forename: Simon E
authors.initials: SE
authors.lastname: Lewis
mesh_terms: D002384:Catalysis; D053138:Cyclohexenes / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D010083:Oxidants, Photochemical / Q000737:chemistry*; D010084:Oxidation-Reduction; D010545:Peroxides / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: C573511:3-O-debenzoylzeylenone; D053138:Cyclohexenes; D010083:Oxidants, Photochemical; D010545:Peroxides; C573512:zeylenol