American Chemical Society
ol6b01798_si_001.pdf (3.9 MB)

On the Origin of Dolabriferol: Total Synthesis via Its Putative Contiguous Precursor

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journal contribution
posted on 2016-07-13, 17:39 authored by Athanasios Karagiannis, Naveen Diddi, Dale E. Ward
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.