Enantioselective Synthesis of Euonyminol

Martin Tomanik, Zhi Xu, Seth B. Herzon

Research output: Contribution to journalArticlepeer-review


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.

Original languageEnglish (US)
Pages (from-to)699-704
Number of pages6
JournalJournal of the American Chemical Society
Issue number2
StatePublished - Jan 20 2021

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry
  • Biochemistry
  • Colloid and Surface Chemistry


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