title: Unprecedented cobalt-catalyzed isomerization reactions to single skipped 2,4,7-trienes applied in the synthesis of urushiol.
abstract: The cobalt-catalyzed isomerization of 1,3-dienes to 2Z,4E-dienes was realized for the very challenging substrates with an additional double bond in the side chain. An isomerization to the conjugated 3,5,7-triene derivative was not observed, which is in stark contrast to observations with many other isomerization catalysts. Accordingly, the synthesis of the natural product urushiol, which has a sensitive 2Z,4E,7Z-triene subunit in the side chain, was investigated. The O-protected urushiol derivative was generated selectively without isomerization to the conjugated 3,5,7-triene or Z/E-isomerization of the double bond at position 7.
authors.affiliation: Fachbereich Chemie, Philipps-Universität Marburg, Hans-Meerwein-Straße 4, 35043 Marburg (Germany), Fax: (+49) 6421 2825677.
authors.forename: Anastasia
authors.initials: A
authors.lastname: Schmidt
authors.forename: Gerhard
authors.initials: G
authors.lastname: Hilt
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D002384:Catalysis; D002396:Catechols / Q000138:chemical synthesis* / Q000737:chemistry; D003035:Cobalt / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000466:Alkadienes; D002396:Catechols; D003035:Cobalt; C003747:urushiol
keywords: 1,3-dienes; cobalt; isomerization; stereoselectivity; urushiol