title: Double cycloisomerization as a novel and expeditious route to tricyclic heteroaromatic compounds: short and highly diastereoselective synthesis of (+/-)-tetraponerine T6.
abstract: [reaction: see text] Cu-Assisted double cycloisomerization of bis-alkynylpyrimidines afforded the 5-6-5 tricyclic heteroaromatic skeleton. This transformation was used as a key step in the highly diastereoselective total synthesis of (+/-)-tetraponerine T6.
authors.affiliation: Department of Chemistry, University of Illinois at Chicago, 875 West Taylor Street, Chicago, Illinois 60607-7061, USA.
authors.forename: Joseph T
authors.initials: JT
authors.lastname: Kim
authors.forename: Vladimir
authors.initials: V
authors.lastname: Gevorgyan
mesh_terms: D004583:Electrons; D006575:Heterocyclic Compounds, 3-Ring / Q000138:chemical synthesis*; D007212:Indolizines / Q000138:chemical synthesis; D011743:Pyrimidines / Q000737:chemistry; D013237:Stereoisomerism; D054836:Indolizidines
chemical_list: D006575:Heterocyclic Compounds, 3-Ring; D007212:Indolizines; D011743:Pyrimidines; C110223:indolizidine-195B; C475971:tetraponerine T6; D054836:Indolizidines