Abstract

AbstractOur 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.

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