title: Electronic-state switching strategy in the photochemical synthesis of indanones from o-methyl phenacyl epoxides.
abstract: An electronic excited-state switching strategy has been utilized to control the selectivity of a key photochemical step in the total synthesis of indanorine. The excited-state character of 4,5-dimethoxy-2-methylphenacyl epoxide was changed from an unfavorable (3)π,π* state to a productive (3)n,π* state by a temporary structural modification, resulting in a relatively efficient and high-yielding formation of an indanone derivative. The corresponding structural modification was selected on the basis of quantum chemical calculations prior to the synthesis.
authors.affiliation: Department of Chemistry, Faculty of Science, Masaryk University, Kamenice 5/A8, 625 00 Brno, Czech Republic.
authors.forename: Peter
authors.initials: P
authors.lastname: Štacko
authors.forename: Tomáš
authors.initials: T
authors.lastname: Šolomek
authors.forename: Petr
authors.initials: P
authors.lastname: Klán