On the Origin of Dolabriferol: Total Synthesis via Its Putative Contiguous Precursor.
Τίτλος | On the Origin of Dolabriferol: Total Synthesis via Its Putative Contiguous Precursor. |
Publication Type | Journal Article |
Year of Publication | 2016 |
Authors | Karagiannis, A., Diddi N., & Ward D. E. |
Journal | Org Lett |
Volume | 18 |
Issue | 15 |
Pagination | 3794-7 |
Date Published | 2016 08 05 |
ISSN | 1523-7052 |
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. |
DOI | 10.1021/acs.orglett.6b01798 |
Alternate Journal | Org. Lett. |
PubMed ID | 27410168 |