Enantioselective Synthesis of Euonyminol

J Am Chem Soc. 2021 Jan 20;143(2):699-704. doi: 10.1021/jacs.0c12998. Epub 2021 Jan 7.


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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.