title: Synthesis of the tetracyclic core of berkelic acid using gold(I)-catalyzed hydroarylation and oxidative radical cyclizations.
abstract: A synthetic approach to the tetracyclic core of berkelic acid is reported using gold(I)-catalyzed intramolecular hydroarylation and oxidative radical cyclizations to effect the key ring-forming steps. The carboxylic acid was introduced via a late-stage palladium-catalyzed carbonylation to afford the core tetracycle with the correct relative stereochemistry for the natural product.
authors.affiliation: School of Chemical Sciences, The University of Auckland, 23 Symonds Street, Auckland, New Zealand. m.brimble@auckland.ac.nz
authors.forename: Margaret A
authors.initials: MA
authors.lastname: Brimble
authors.forename: Isabell
authors.initials: I
authors.lastname: Haym
authors.forename: Jonathan
authors.initials: J
authors.lastname: Sperry
authors.forename: Daniel P
authors.initials: DP
authors.lastname: Furkert
mesh_terms: D002384:Catalysis; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013141:Spiro Compounds / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D013141:Spiro Compounds; C520589:berkelic acid; D006046:Gold