Abstract
( E)-5-Tosyl-4-pentenoic acid ( 9), prepared from 4-pentenoic acid by stereoselective in situ iodosulfonylation-dehydroiodimation, is lithiated at vinylic position and reacts with carbonyl compounds affording stereoselectively 6-hydroxy acids 12. These acids have been stereoselectively transformed into methyl (2 E,4 E)-6-hydroxydienoates 13, by esterification with trimethylsilyldiazo methane followed by δ-dehydrosulfinylation with DBU, or into ( Z)-γ-lactones 14 by heating in the presence of p-toluenesulfonic acid.
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