title: Studies toward the synthesis of the epoxykinamycin FL-120B': discovery of a decarbonylative photocyclization.
abstract: Photo-Friedel-Crafts acylation of a naphthoquinone was attempted in an effort to access a diazobenzofluorenone en route to the epoxykinamycin natural product FL-120B'. Photoirradiation of the naphthoquinone substrate which resulted in the unexpected formation of a tetracyclic naphthofuran via a decarbonylative photocyclization process is described.
authors.affiliation: Department of Chemistry and Center for Chemical Methodology and Library Development (CMLD), Boston University, Boston, Massachusetts 02215, United States.
authors.forename: Stephen S
authors.initials: SS
authors.lastname: Scully
authors.forename: John A
authors.initials: JA
authors.lastname: Porco
mesh_terms: D000215:Acylation; D001391:Azo Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002227:Carbazoles / Q000138:chemical synthesis / Q000737:chemistry; D003500:Cyclization; D004852:Epoxy Compounds / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D009285:Naphthoquinones / Q000138:chemical synthesis / Q000737:chemistry*; D000095602:Angucyclines and Angucyclinones
chemical_list: D001391:Azo Compounds; D002227:Carbazoles; D004852:Epoxy Compounds; D009285:Naphthoquinones; C515381:kinamycin C; D000095602:Angucyclines and Angucyclinones; C088443:FL 120B'