Selective synthesis of (2Z,4E)-dienyl esters by ene-diene cross metathesis.
[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.
Moura-Letts
Gustavo
G
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Curran
Dennis P
DP
D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry*; D018942:Macrolides / Q000737:chemistry; D015394:Molecular Structure; D012997:Solvents
D004952:Esters; D018942:Macrolides; D012997:Solvents; C470814:dictyostatin