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Oxidative Coupling of â‐ O ‐4′ Dilignol Models Leading to Polycyclic Products with Rare Interlignol Linkages
Author(s) -
Peng Chang,
Liu Wujun,
Ning Siyang,
Ge Guangbo,
Zhao Zongbao K.
Publication year - 2017
Publication title -
asian journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.846
H-Index - 44
eISSN - 2193-5815
pISSN - 2193-5807
DOI - 10.1002/ajoc.201700529
Subject(s) - hypervalent molecule , chemistry , oxidative coupling of methane , oxidative phosphorylation , nonane , reagent , combinatorial chemistry , organic chemistry , catalysis , biochemistry
Our capability to utilize lignin as a renewable resource has been continuously expanding thanks to the information acquired through in‐depth studies with various model compounds. Herein, efficient routes were devised to assemble biomass‐derived building blocks for functionalized â‐ O ‐4′ dilignol models. Oxidative coupling of these dilignols with hypervalent iodine(III) reagents led to two series of highly fused polycyclic products, dibenzo[ b , d ]oxepine and 2,7‐dioxabicyclo[3,3,1]nonane derivatives. These products contain rare interlignol C−C and C−O linkages and are otherwise difficult to synthesize. Preliminary studies suggested that some of these products had moderate anticancer activity.