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

Philip G. E. Craven; Richard J. K. Taylor

doi:10.1055/s-0032-1318130

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

Philip G. E. Craven, Richard J. K. Taylor^*

^*Corresponding author for this work

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

Mild and efficient routes to (E,E)-and (E,Z)-4-methoxypentadienoic acid esters from readily accessible gamma,delta-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.

Original language	English
Article number	ST-2012-D1095-L
Pages (from-to)	363-368
Number of pages	6
Journal	Synlett
Volume	24
Issue number	3
DOIs	https://doi.org/10.1055/s-0032-1318130
Publication status	Published - Feb 2013

Keywords

acid catalysis
palladium catalysis
ESTERS
epoxides
stereoselective synthesis
diene synthesis

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10.1055/s-0032-1318130

https://www.thieme-connect.de/DOI/DOI?10.1055/s-0032-1318130

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N2 - Mild and efficient routes to (E,E)-and (E,Z)-4-methoxypentadienoic acid esters from readily accessible gamma,delta-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.

AB - Mild and efficient routes to (E,E)-and (E,Z)-4-methoxypentadienoic acid esters from readily accessible gamma,delta-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.

KW - acid catalysis

KW - palladium catalysis

KW - ESTERS

KW - epoxides

KW - stereoselective synthesis

KW - diene synthesis

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ER -

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

Abstract

Keywords

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