@article{oai:nagasaki-u.repo.nii.ac.jp:00002617, author = {Matsuo, Yosuke and Yoshida, Ayane and Saito, Yoshinori and Tanaka, Takashi}, issue = {39}, journal = {Angewandte Chemie International Edition}, month = {Sep}, note = {Goupiolones?A and B are unique phenolic compounds with significant DNA-damaging activity. In this study, the structure of goupiolone?B was revised on the basis of DFT calculations of the 13C?NMR chemical shifts and biosynthetic considerations. The dibenzobicyclo[3.2.2]nonane skeleton of the revised structure suggested that goupiolone?B was produced by oxidative coupling between catechol and goupiolone?A, which was strongly supported by biomimetic synthesis. Furthermore, racemization of goupiolone?B was observed during the attempted resolution of its racemic mixture. A plausible racemization mechanism involving α-ketol rearrangement is proposed., Angewandte Chemie International Edition, 56(39), pp.11855-11859; 2017}, pages = {11855--11859}, title = {Structural Revision and Biomimetic Synthesis of Goupiolone?B}, volume = {56}, year = {2017} }