New research paper from the Thomas Poulsen lab published in Angewandte Chemie

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

2018.06.12 | Susan Hjort Skyum

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. Here, we show that Co(OAc)2 and Mn(OAc)3•2H2O 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.


Authors: Wanwan Yu, Per Hjerrild, Kristian M. Jacobsen, Henriette N. Tobiesen, Line Clemmensen, Thomas B. Poulsen

Department of Chemistry, Staff, Public / media