title: A ring-expansion approach to roseophilin.
abstract: [reaction: see text] Preparation of a cyclopentenone-fused pyrrolophane, which serves as a model for the tricyclic core of roseophilin (1), is described. The synthetic scheme features a palladium-catalyzed annulation and oxidative cleavage sequence to provide a macrocyclic ketoester (17). Modified Paal-Knorr pyrrole synthesis and Friedel-Crafts acylation complete the pyrrolophane model system (20).
authors.affiliation: Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.
authors.forename: Samuel G
authors.initials: SG
authors.lastname: Salamone
authors.forename: Gregory B
authors.initials: GB
authors.lastname: Dudley
mesh_terms: D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry; D007659:Ketones / Q000737:chemistry; D015394:Molecular Structure; D010084:Oxidation-Reduction; D011353:Prodigiosin / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D007659:Ketones; D011758:Pyrroles; C408872:roseophilin; D011353:Prodigiosin