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Unified Synthesis of 2-Isocyanoallopupukeanane and 9-Isocyanopupukeanane through a "Contra-biosynthetic" Rearrangement.
Hardy, Melissa A; Hayward Cooke, Jack; Feng, Zhitao; Noda, Kenta; Kerschgens, Isabel; Massey, Lynée A; Tantillo, Dean J; Sarpong, Richmond.
  • Hardy MA; Department of Chemistry, University of California, Berkeley, CA 94720, USA.
  • Hayward Cooke J; Department of Chemistry, University of California, Berkeley, CA 94720, USA.
  • Feng Z; Department of Chemistry, University of California, Davis, CA 95616, USA.
  • Noda K; Department of Chemistry, University of California, Berkeley, CA 94720, USA.
  • Kerschgens I; Department of Chemistry, University of California, Berkeley, CA 94720, USA.
  • Massey LA; Department of Chemistry, University of California, Berkeley, CA 94720, USA.
  • Tantillo DJ; Department of Chemistry, University of California, Davis, CA 95616, USA.
  • Sarpong R; Department of Chemistry, University of California, Berkeley, CA 94720, USA.
Angew Chem Int Ed Engl ; 63(4): e202317348, 2024 Jan 22.
Article en En | MEDLINE | ID: mdl-38032339
Herein, we describe our synthetic efforts toward the pupukeanane natural products, in which we have completed the first enantiospecific route to 2-isocyanoallopupukeanane in 10 steps (formal synthesis), enabled by a key Pd-mediated cyclization cascade. This subsequently facilitated an unprecedented bio-inspired "contra-biosynthetic" rearrangement, providing divergent access to 9-isocyanopupukeanane in 15 steps (formal synthesis). Computational studies provide insight into the nature of this rearrangement.
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Texto completo: 1 Banco de datos: MEDLINE Idioma: En Año: 2024 Tipo del documento: Article
Texto completo
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Texto completo: 1 Banco de datos: MEDLINE Idioma: En Año: 2024 Tipo del documento: Article