title: Synthesis of a 1,3-Bridged Macrobicyclic Enyne via Chemoselective Cycloisomerization Using Palladium-Catalyzed Alkyne-Alkyne Coupling.
abstract: A unique intramolecular Pd-catalyzed alkyne-alkyne coupling is presented. This transformation generates a strained, 1,3-bridged, macrocyclic enyne. The process was readily executed on gram scale, and the structure of the product was elucidated via X-ray crystallographic analysis. A mechanistic rationale for the observed chemoselectivity is provided.
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305-4401, United States.
authors.forename: Barry M
authors.initials: BM
authors.lastname: Trost
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305-4401, United States.
authors.forename: James T
authors.initials: JT
authors.lastname: Masters
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305-4401, United States.
authors.forename: Franck
authors.initials: F
authors.lastname: Le Vaillant
authors.affiliation: Department of Chemistry, Stanford University , Stanford, California 94305-4401, United States.
authors.forename: Jean-Philip
authors.initials: JP
authors.lastname: Lumb
mesh_terms: D000480:Alkynes / Q000737:chemistry*; D018360:Crystallography, X-Ray; D003500:Cyclization; D047028:Macrocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D013058:Mass Spectrometry; D010165:Palladium / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000480:Alkynes; D047028:Macrocyclic Compounds; D010165:Palladium