title: Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis.
abstract: [reaction: see text] Cross metathesis of terminal alkenes with methyl (2Z,4E)-hexadienoate and related dienyl esters provides substituted (2Z,4E)-dienyl esters in good yields. Small-scale reactions are effectively promoted by the standard second-generation Grubbs-Hoveyda catalyst (GH-II), while a new fluorous GH-II catalyst is used for separation and recovery in gram-scale reactions. The transformation is featured in a rapid synthesis of the bottom fragments of the potent anticancer agents (-)-dictyostatin and 6-epi-dictyostatin.
authors.affiliation: Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
authors.forename: Gustavo
authors.initials: G
authors.lastname: Moura-Letts
authors.forename: Dennis P
authors.initials: DP
authors.lastname: Curran
mesh_terms: D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D018942:Macrolides / Q000737:chemistry; D015394:Molecular Structure; D012997:Solvents
chemical_list: D004952:Esters; D018942:Macrolides; D012997:Solvents; C470814:dictyostatin