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Total Synthesis and Late‐Stage C−H Oxidations of ent‐Trachylobane Natural Products

Wein, Lukas Anton ; Wurst, Klaus ; Magauer, Thomas

Angewandte Chemie (International ed.), 2022-01, Vol.61 (3), p.e202113829-n/a [Periódico revisado por pares]

Germany: Wiley Subscription Services, Inc

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  • Título:
    Total Synthesis and Late‐Stage C−H Oxidations of ent‐Trachylobane Natural Products
  • Autor: Wein, Lukas Anton ; Wurst, Klaus ; Magauer, Thomas
  • Assuntos: Biomimetic synthesis ; Chemical synthesis ; C−H activation ; Diterpenes ; Enantiomers ; Natural products ; Oxidation ; Terpenoids ; Total synthesis
  • É parte de: Angewandte Chemie (International ed.), 2022-01, Vol.61 (3), p.e202113829-n/a
  • Notas: ObjectType-Article-1
    SourceType-Scholarly Journals-1
    ObjectType-Feature-2
    content type line 23
  • Descrição: Herein, we present our studies to construct seven ent‐trachylobane diterpenoids by employing a bioinspired two‐phase synthetic strategy. The first phase provided enantioselective and scalable access to five ent‐trachylobanes, of which methyl ent‐trachyloban‐19‐oate was produced on a 300 mg scale. During the second phase, chemical C−H oxidation methods were employed to enable selective conversion to two naturally occurring higher functionalized ent‐trachylobanes. The formation of regioisomeric analogs, which are currently inaccessible via enzymatic methods, reveals the potential as well as limitations of established chemical C−H oxidation protocols for complex molecule synthesis. We report an asymmetric synthesis of several ent‐trachylobane diterpenoids. The developed strategy is based on the two‐phase terpenoid synthesis concept and involves carbon framework assembly (Cyclase Phase) and aliphatic C−H oxidation (Oxidase Phase). This enabled access to seven natural products and diverse non‐natural analogs that were previously inaccessible via enzymatic and/or chemical methods. The robustness of the chemistry was demonstrated by preparing 300 mg of methyl ent‐trachyloban‐19‐oate.
  • Editor: Germany: Wiley Subscription Services, Inc
  • Idioma: Inglês
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  • Realização: ABCD-USP USP   Logos de Redes Sociais: Freepik

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