title: 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) 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.
authors.affiliation: Department of Chemistry and Chemical Biology, McMaster University Faculty of Science , Hamilton, Ontario , Canada L8S 4M1.
authors.forename: David
authors.initials: D
authors.lastname: McLeod
authors.affiliation: Department of Chemistry and Chemical Biology, McMaster University Faculty of Science , Hamilton, Ontario , Canada L8S 4M1.
authors.forename: James
authors.identifier: 0000-0002-7123-7588
authors.initials: J
authors.lastname: McNulty
keywords: macrolactones; synthetic methodology; total synthesis