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Published on: July 9, 2015
A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine-26
Wanwan Yu1, Per Hjerrild1, Kristian M Jacobsen1
1Department of Chemistry, Aarhus University, Langelandsgade 140, 8000, Aarhus C, Denmark.
Abstract:
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 H2 O 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.
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