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Synthesis of Coprinol and Several Alcyopterosin Sesquiterpenes by Regioselective [2 + 2 + 2] Alkyne Cyclotrimerization.
Tavakoli, Amir; Dudley, Gregory B.
Afiliación
  • Tavakoli A; C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26505, United States.
  • Dudley GB; C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, West Virginia 26505, United States.
J Org Chem ; 87(21): 14909-14914, 2022 11 04.
Article en En | MEDLINE | ID: mdl-36215202
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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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Sesquiterpenos / Alquinos Idioma: En Revista: J Org Chem Año: 2022 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos
Texto completo
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XML
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Sesquiterpenos / Alquinos Idioma: En Revista: J Org Chem Año: 2022 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Estados Unidos