The Royal Society, Royal Society Open Science, 11(3), p. 160374, 2016
DOI: 10.1098/rsos.160374
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Advances on the use of the 2-pinacolacetal-tripropylphosphonium salt DualPhos as a general reagent for the two-carbon aldehyde to alkenal homologation and a chemoselective iron (III) chloride mediated deprotection are described. The strategy allows isolation of the latent alkenal intermediates or direct hydrolysis to ( E )-alkenals. The robust chemical stability of the latent alkenals is demonstrated in a total synthesis of the macrolactone phomolide G.