title: Modular access to complex prodiginines: total synthesis of (+)-roseophilin via its 2-azafulvene prototropisomer.
abstract: Ansa-bridged prodiginines are bioactive pigments produced by bacteria. Certain of these structures are reported to be antagonists of protein-protein interactions involved in apoptosis. We describe a new entry to alkaloids of this type, demonstrated with a concise asymmetric synthesis of (+)-roseophilin (3). Our route constructs the pyrrolophane motif via phosphoryl transfer-terminated macroaldolization and passes through a previously unexplored prototropic form of the natural product.
authors: Department of Chemistry and Biochemistry, University of California, Los Angeles, 607 Charles E. Young Drive East, Los Angeles, California 90095-1569, USA.
authors: James H
authors: JH
authors: Frederich
authors: Patrick G
authors: PG
authors: Harran
mesh_terms: D001372:Aza Compounds / Q000737:chemistry*; D003517:Cyclopentanes / Q000737:chemistry*; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry; D015394:Molecular Structure; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: C583096:2-azafulvene; D001372:Aza Compounds; D003517:Cyclopentanes; D006575:Heterocyclic Compounds, 3-Ring; D011758:Pyrroles; C408872:roseophilin