Enantioselective Synthesis of Euonyminol
- 7 January 2021
- journal article
- research article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 143 (2), 699-704
- https://doi.org/10.1021/jacs.0c12998
Abstract
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.Funding Information
- Yale University
- National Science Foundation (CHE- 1954319)
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