title: Direct and short construction of the ACDE ring system of daphenylline.
abstract: Daphenylline, a novel daphniphyllum alkaloid, boasts a fused and bridging ring system coupled with six stereogenic centers. Here we present a direct and short construction of the ACDE ring system of daphenylline from the known 3-(2-bromophenyl)propanal in 10 steps and 17 % overall yield. The synthesis features an iron(III)-catalyzed aza-Cope-Mannich reaction, a self-terminating 6-exo-trig aryl radical-alkene cyclization and an intramolecular Friedel-Crafts acylation.
authors.affiliation: State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, 730000 (P. R. China).
authors.forename: Wei
authors.initials: W
authors.lastname: Wang
authors.forename: Guo-Ping
authors.initials: GP
authors.lastname: Li
authors.forename: Shao-Feng
authors.initials: SF
authors.lastname: Wang
authors.forename: Zi-Fa
authors.initials: ZF
authors.lastname: Shi
authors.forename: Xiao-Ping
authors.initials: XP
authors.lastname: Cao
mesh_terms: D000215:Acylation; D000447:Aldehydes / Q000737:chemistry; D000470:Alkaloids / Q000138:chemical synthesis / Q000737:chemistry*; D000475:Alkenes / Q000737:chemistry; D002384:Catalysis; D047248:Crown Compounds / Q000737:chemistry; D018360:Crystallography, X-Ray; D003500:Cyclization; D005290:Ferric Compounds / Q000737:chemistry; D008968:Molecular Conformation
chemical_list: D000447:Aldehydes; D000470:Alkaloids; D000475:Alkenes; D047248:Crown Compounds; D005290:Ferric Compounds; C541594:daphenylline; C005556:propionaldehyde
keywords: Friedel-Crafts acylation; alkaloids; aza-Cope-Mannich reaction; cyclization; daphenylline