A Catalytic Oxidative Quinone Heterofunctionalization Method:Synthesis of Strongylophorine-26
Autor: | Wanwan Yu, Kristian M. Jacobsen, Henriette N. Tobiesen, Line Clemmensen, Thomas B. Poulsen, Per Hjerrild |
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Jazyk: | angličtina |
Rok vydání: | 2018 |
Předmět: |
quinones
Natural product 010405 organic chemistry Chemistry natural products oxidation Heteroatom General Medicine General Chemistry 010402 general chemistry 01 natural sciences Combinatorial chemistry cobalt Catalysis 0104 chemical sciences Quinone chemistry.chemical_compound Nucleophile terpenoids Surface modification Moiety Reactivity (chemistry) |
Zdroj: | Yu, W, Hjerrild, P, Jacobsen, K M, Tobiesen, H N, Clemmensen, L & Poulsen, T B 2018, ' A Catalytic Oxidative Quinone Heterofunctionalization Method : Synthesis of Strongylophorine-26 ', Angewandte Chemie-International Edition, vol. 57, no. 31, pp. 9805-9809 . https://doi.org/10.1002/anie.201805580 |
DOI: | 10.1002/anie.201805580 |
Popis: | The preparation of heteroatom-substituted p-quinones is ideally performed by direct addition of a nucleophile followed by in situ reoxidation. Albeit an appealing strategy, the reactivity of the p-quinone moiety is not easily tamed and no broadly applicable method for heteroatom functionalization exists. Shown herein is that Co(OAc)2 and Mn(OAc)3⋅2 H2O act as powerful catalysts for oxidative p-quinone functionalization with a collection of O, N, and S nucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine-26 is presented. |
Databáze: | OpenAIRE |
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