AI Article Synopsis
- Successfully completed an asymmetric total synthesis of guignardones A and B.
- The synthesis involved constructing a complex 6-oxabicyclo[3.2.1]octane structure starting from d-quinic acid through a series of targeted chemical reactions.
- Key transformations included a Pummerer rearrangement, 1,4-addition/elimination, and a final Knoevenagel condensation followed by dehydration to obtain both guignardone compounds.
Article Abstract
The asymmetric total synthesis of (-)-guignardones A () and B () has been accomplished. The highly oxidized 6-oxabicyclo[3.2.1]octane core was constructed from d-quinic acid via substitution/desulfurization reaction with thiophenol to forge the bridged ring scaffold, and a Pummerer rearrangement and 1,4-addition/elimination sequence was employed to install the β-carbonyl group at the congested C-1 position. A late-stage Knoevenagel condensation-6π-electrocyclization and directed hydrogenation formed (-)-guignardone B (), which was subjected to dehydration to furnish (-)-guignardone A ().
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| http://dx.doi.org/10.1021/acs.orglett.0c00241 | DOI Listing |
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