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

摘要

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)2H(2)O act as powerful catalysts for oxidative p-quinone functionalization with a collection of O, N, and Snucleophiles, using oxygen as the terminal oxidant. Preliminary mechanistic observations and the first synthesis of the cytotoxic natural product strongylophorine-26 is presented.