Enantioselective Synthesis of Euonyminol

We describe an enantioselective total synthesis of the nonahydroxylated sesquiterpenoid euonyminol, the dihydro-β-agarofuran nucleus of the macrocyclic terpenoid alkaloids known as the cathedulins. Key features of the synthetic sequence include a highly diastereoselective intramolecular alkene oxyal...

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Bibliographic Details
Published in:Journal of the American Chemical Society 2021-01, Vol.143 (2), p.699-704
Main Authors: Tomanik, Martin, Xu, Zhi, Herzon, Seth B
Format: Article
Language:English
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Summary:We describe an enantioselective total synthesis of the nonahydroxylated sesquiterpenoid euonyminol, the dihydro-β-agarofuran nucleus of the macrocyclic terpenoid alkaloids known as the cathedulins. Key features of the synthetic sequence include a highly diastereoselective intramolecular alkene oxyalkylation to establish the C10 quaternary center, an intramolecular aldol–dehydration to access the tricyclic scaffold of the target, a tandem lactonization–epoxide opening to form the trans-C2–C3 vicinal diol residue, and a late-stage diastereoselective α-ketol rearrangement. The synthesis provides the first synthetic access to enantioenriched euonyminol and establishes a platform to synthesize the cathedulins.
ISSN:0002-7863
1520-5126
DOI:10.1021/jacs.0c12998