title: On the Origin of Dolabriferol: Total Synthesis via Its Putative Contiguous Precursor.
abstract: The putative contiguous polypropionate precursor of dolabriferol was synthesized using as the key step a rationally designed enantiomer-selective aldol coupling (i.e., with kinetic resolution) of a racemic C1-C8 ketone fragment with an enantiopure C9-C15 aldehyde fragment. When exposed to alumina, the precursor was cleanly transformed into dolabriferol via a regioselective retro-Claisen fragmentation, providing the first experimental evidence for the proposed origin of dolabriferol and demonstrating that it is a plausible isolation artifact.
authors.affiliation: Department of Chemistry, University of Saskatchewan , 110 Science Place, Saskatoon, SK S7N 5C9, Canada.
authors.forename: Athanasios
authors.initials: A
authors.lastname: Karagiannis
authors.affiliation: Department of Chemistry, University of Saskatchewan , 110 Science Place, Saskatoon, SK S7N 5C9, Canada.
authors.forename: Naveen
authors.initials: N
authors.lastname: Diddi
authors.affiliation: Department of Chemistry, University of Saskatchewan , 110 Science Place, Saskatoon, SK S7N 5C9, Canada.
authors.forename: Dale E
authors.initials: DE
authors.lastname: Ward