title: Novel reaction pathways for 2-pyridone [4+4] photoadducts.
abstract: [Structure: see text] Transannular ring closure of a pyridone-furan [4+4] photoadduct has been evaluated in a model system. A combination of nitrogen substitution and an isopropyl group gave full control of the four new stereogenic centers. Chlorination transformed the 1,5-cyclooctadiene to a [4.2.0] ring system instead of to the expected [3.3.0] ring system. Changing an alkene to an enone suppressed this pathway and led to a new rearrangement, converting the 5-8-5 ring system to a 6-7-5 system.
authors.affiliation: Department of Chemistry, Temple University, Philadelphia, Pennsylvania 19010, USA.
authors.forename: Peiling
authors.initials: P
authors.lastname: Chen
authors.forename: Yanping
authors.initials: Y
authors.lastname: Chen
authors.forename: Patrick J
authors.initials: PJ
authors.lastname: Carroll
authors.forename: Scott McN
authors.initials: SM
authors.lastname: Sieburth