title: Nucleophile- or light-induced synthesis of 3-substituted phthalides from 2-formylarylketones.
abstract: The surprisingly facile conversion (isomerization) of 2-formyl-arylketones into 3-substituted phthalides, as observed for the marine natural product pestalone and its per-O-methylated derivative, was investigated using a series of simple 2-acylbenzaldehydes as substrates. The transformation generally proceeds smoothly in DMSO, either in a Cannizarro-Tishchenko-type reaction under nucleophile catalysis (NaCN) or under photochemical conditions (DMSO, 350 nm).
authors.affiliation: Department of Chemistry, University of Cologne, Greinstr. 4, 50939 Köln, Germany.
authors.forename: Dario C
authors.initials: DC
authors.lastname: Gerbino
authors.forename: Daniel
authors.initials: D
authors.lastname: Augner
authors.forename: Nikolay
authors.initials: N
authors.lastname: Slavov
authors.forename: Hans-Günther
authors.initials: HG
authors.lastname: Schmalz
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D001577:Benzophenones / Q000737:chemistry*; D001688:Biological Products / Q000737:chemistry*; D002384:Catalysis; D004121:Dimethyl Sulfoxide / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008027:Light; D015394:Molecular Structure
chemical_list: D001572:Benzofurans; D001577:Benzophenones; D001688:Biological Products; D007659:Ketones; C442628:pestalone; C082022:phthalide; D004121:Dimethyl Sulfoxide