Biomimetic synthesis of (-)-longithorone A

J Am Chem Soc. 2002 Feb 6;124(5):773-5. doi: 10.1021/ja016585u.


An enantioseletive, biomimetic synthesis of (-)-longithorone A has been achieved using an intermolecular/transannular Diels-Alder sequence which provides some support for the proposed biosynthesis. The cycloaddition precursors were two [12]-paracyclophanes that were constructed with atropisomer control during ene-yne metathesis macrocyclizations.

Publication types

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

MeSH terms

  • Biological Factors / chemical synthesis*
  • Bridged-Ring Compounds / chemical synthesis*
  • Molecular Mimicry
  • Polycyclic Compounds / chemical synthesis*
  • Stereoisomerism


  • Biological Factors
  • Bridged-Ring Compounds
  • Polycyclic Compounds
  • longithorone A