DualPhos: A versatile, chemoselective reagent for two-carbon aldehyde to latent (E)-alkenal homologation and application in the total synthesis of phomolide G

Abstract

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) chloridemediated 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.