A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26

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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.

OriginalsprogEngelsk
TidsskriftAngewandte Chemie - International Edition
Vol/bind57
Nummer31
Sider (fra-til)9805-9809
Antal sider5
ISSN1433-7851
DOI
StatusUdgivet - 26 jul. 2018

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