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E- and Z-trisubstituted macrocyclic alkenes for natural product synthesis and skeletal editing.
Mu, Yucheng; Hartrampf, Felix W W; Yu, Elsie C; Lounsbury, Katherine E; Schrock, Richard R; Romiti, Filippo; Hoveyda, Amir H.
Afiliación
  • Mu Y; Merkert Chemistry Center, Boston College, Chestnut Hill, MA, USA.
  • Hartrampf FWW; Merkert Chemistry Center, Boston College, Chestnut Hill, MA, USA.
  • Yu EC; Merkert Chemistry Center, Boston College, Chestnut Hill, MA, USA.
  • Lounsbury KE; Supramolecular Science and Engineering Institute, University of Strasbourg and CNRS, Strasbourg, France.
  • Schrock RR; Department of Chemistry, Massachusetts Institute of Technology, Cambridge, MA, USA.
  • Romiti F; Merkert Chemistry Center, Boston College, Chestnut Hill, MA, USA. romiti@unistra.fr.
  • Hoveyda AH; Supramolecular Science and Engineering Institute, University of Strasbourg and CNRS, Strasbourg, France. romiti@unistra.fr.
Nat Chem ; 14(6): 640-649, 2022 06.
Article en En | MEDLINE | ID: mdl-35577918
Many therapeutic agents are macrocyclic trisubstituted alkenes but preparation of these structures is typically inefficient and non-selective. A possible solution would entail catalytic macrocyclic ring-closing metathesis, but these transformations require high catalyst loading, conformationally rigid precursors and are often low yielding and/or non-stereoselective. Here we introduce a ring-closing metathesis strategy for synthesis of trisubstituted macrocyclic olefins in either stereoisomeric form, regardless of the level of entropic assistance. The goal was achieved by addressing several unexpected difficulties, including complications arising from pre-ring-closing metathesis alkene isomerization. The power of the method is highlighted by two examples. The first is the near-complete reversal of substrate-controlled selectivity in the formation of a macrolactam related to an antifungal natural product. The other is a late-stage stereoselective generation of an E-trisubstituted alkene in a 24-membered ring, en route to the cytotoxic natural product dolabelide C.
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Productos Biológicos / Alquenos Idioma: En Revista: Nat Chem Asunto de la revista: QUIMICA Año: 2022 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Reino Unido
Texto completo
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Texto completo: 1 Colección: 01-internacional Base de datos: MEDLINE Asunto principal: Productos Biológicos / Alquenos Idioma: En Revista: Nat Chem Asunto de la revista: QUIMICA Año: 2022 Tipo del documento: Article País de afiliación: Estados Unidos Pais de publicación: Reino Unido