Formal synthesis of (+/-)-roseophilin.
A formal synthesis of (+/-)-roseophilin is described. Scandium(III)-catalyzed Nazarov cyclization of 2,5-disubstituted N-tosylpyrrole 19 gives a 5,5'-fused ketopyrrole, and ansa-bridge formation via pi-allyl palladium macrocyclization gives 21.
Bitar
Abdallah Y
AY
Department of Chemistry, University of Rochester, Rochester, New York 14627, USA.
Frontier
Alison J
AJ
D000970:Antineoplastic Agents / Q000138:chemical synthesis / Q000737:chemistry; D002384:Catalysis; D018360:Crystallography, X-Ray; D003500:Cyclization; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D009942:Organometallic Compounds / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry; D012538:Scandium / Q000737:chemistry; D013237:Stereoisomerism
D000970:Antineoplastic Agents; D006575:Heterocyclic Compounds, 3-Ring; D009942:Organometallic Compounds; D011758:Pyrroles; C408872:roseophilin; D012538:Scandium