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.

Department of Chemistry Faculty of Science Masaryk University Kamenice 5 A8 625 00 Brno Czech Republic

Citace poskytuje Crossref.org

Photoremovable protecting groups in chemistry and biology: reaction mechanisms and efficacy