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A Catalytic Oxidative Quinone Heterofunctionalization Method: Synthesis of Strongylophorine‐26
Author(s) -
Yu Wanwan,
Hjerrild Per,
Jacobsen Kristian M.,
Tobiesen Henriette N.,
Clemmensen Line,
Poulsen Thomas B.
Publication year - 2018
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201805580
Subject(s) - moiety , nucleophile , quinone , chemistry , heteroatom , catalysis , reactivity (psychology) , combinatorial chemistry , surface modification , natural product , oxidative phosphorylation , organic chemistry , ring (chemistry) , biochemistry , medicine , alternative medicine , pathology
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 H 2 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.