A ring-expansion approach to roseophilin.
[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).
Salamone
Samuel G
SG
Department of Chemistry and Biochemistry, Florida State University, Tallahassee, Florida 32306-4390, USA.
Dudley
Gregory B
GB
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
D006575:Heterocyclic Compounds, 3-Ring; D007659:Ketones; D011758:Pyrroles; C408872:roseophilin; D011353:Prodigiosin