Stereocontrolled Routes to 4-Methoxypentadienoates for Use in Natural Product Synthesis

PGE Craven, RJK Taylor - Synlett, 2013 - thieme-connect.com
PGE Craven, RJK Taylor
Synlett, 2013thieme-connect.com
Mild and efficient routes to (E, E)-and (E, Z)-4-methoxypentadienoic acid esters from readily
accessible γ, δ-epoxydienoates are described. The crucial epoxide methanolysis can be
carried out in stereocomplementary ways by the use of either acid-mediated or palladium-
catalysed procedures, the latter procedure proving preferable in most cases.
Mild and efficient routes to (E,E)- and (E,Z)-4-methoxypentadienoic acid esters from readily accessible γ,δ-epoxydienoates are described. The crucial epoxide methanolysis can be carried out in stereocomplementary ways by the use of either acid-mediated or palladium-catalysed procedures, the latter procedure proving preferable in most cases.
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