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Updated: Aug 26, 2025

Preparation of a Corannulene-functionalized Hexahelicene by CopperI-catalyzed Alkyne-azide Cycloaddition of Nonplanar Polyaromatic Units
Published on: September 18, 2016
Synthesis of Coprinol and Several Alcyopterosin Sesquiterpenes by Regioselective [2 + 2 + 2] Alkyne
Amir Tavakoli1, Gregory B Dudley1
1C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26505, United States.
Abstract:
Alkyne [2 + 2 + 2] cyclotrimerization is a strategically attractive but tactically challenging approach to the synthesis of highly substituted benzene rings. Here, a bimolecular regioselective cyclotrimerization is applied to the total synthesis of the natural product coprinol and several related alcyopterosins from the illudalane family of sesquiterpenes. The synthesis of coprinol from dimedone was completed in six steps and a 57% overall yield. Alternative functional group manipulations lead to alcyopterosins A, B, and O and two additional congeners, all within six steps.
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