title: Palladium-catalyzed 1,4-difunctionalization of butadiene to form skipped polyenes.
abstract: A palladium-catalyzed 1,4-addition across the commodity chemical 1,3-butadiene to afford skipped polyene products is reported. Through a palladium σ → π → σ allyl isomerization, two new carbon-carbon bonds are formed with high regioselectivity and trans stereoselectivity of the newly formed alkene. The utility of this method is highlighted by the successful synthesis of the ripostatin A skipped triene core.
authors.affiliation: Department of Chemistry, University of Utah, 315 South 1400 East, Salt Lake City, Utah 84112, USA.
authors.forename: Matthew S
authors.initials: MS
authors.lastname: McCammant
authors.forename: Longyan
authors.initials: L
authors.lastname: Liao
authors.forename: Matthew S
authors.initials: MS
authors.lastname: Sigman
mesh_terms: D002070:Butadienes / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D012321:DNA-Directed RNA Polymerases / Q000037:antagonists & inhibitors; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D010165:Palladium / Q000737:chemistry*; D011090:Polyenes / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D002070:Butadienes; D007783:Lactones; D011090:Polyenes; C096600:ripostatin A; D010165:Palladium; D012321:DNA-Directed RNA Polymerases; C031763:1,3-butadiene