title: Gold-Catalyzed Sequential Cyclization of 1-En-3,9-Diyne Esters to Partially Hydrogenated 3H-Dicyclopenta[a,b]naphthalenes.
abstract: A synthetic method that relies on a gold(I)-catalyzed cycloisomerization of 1-en-3,9-diyne esters to spiro[4.4]non-2-ene-substituted 1,2-dihydronaphthalenes is described. Robust with a wide variety of substitution patterns tolerated, the reaction provides the first example of a one-step strategy to construct such novel and architecturally challenging members of the carbocycle family in good to excellent yields. A mechanism is proposed in which the sequential cycloisomerization pathway was thought to involve a gold-catalyzed 1,3-acyloxy migration/Nazarov cyclization followed by a formal [4+2] cycloaddition to give the tetracarbocyclic product.
authors.affiliation: Jiangsu Key Laboratory of Biomass-based Green Fuels and Chemicals, College of Chemical Engineering, Nanjing Forestry University, Nanjing, 210037, P. R. China. weidong@njfu.edu.cn.
authors.forename: Weidong
authors.initials: W
authors.lastname: Rao
authors.affiliation: School of Chemistry, Monash University, Clayton, Victoria, 3800, Australia.
authors.forename: Joshua William
authors.initials: JW
authors.lastname: Boyle
authors.affiliation: School of Chemistry, Monash University, Clayton, Victoria, 3800, Australia. phil.chan@monash.edu, P.W.H.Chan@warwick.ac.uk.|Department of Chemistry, University of Warwick, Coventry, CV4 7AL, UK. phil.chan@monash.edu, P.W.H.Chan@warwick.ac.uk.
authors.forename: Philip Wai Hong
authors.initials: PW
authors.lastname: Chan
keywords: carbocycles; cycloisomerization; gold; homogeneous catalysis; synthetic methods