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Structural Revision and Biomimetic Synthesis of Goupiolone B


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Title: Structural Revision and Biomimetic Synthesis of Goupiolone B
Authors: Matsuo, Yosuke / Yoshida, Ayane / Saito, Yoshinori / Tanaka, Takashi
Issue Date: 18-Sep-2017
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA
Citation: Angewandte Chemie International Edition, 56(39), pp.11855-11859; 2017
Abstract: 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.
Keywords: natural products / biomimetic synthesis / structure elucidation / oxidation / rearrangement
URI: http://hdl.handle.net/10069/37836
ISSN: 14337851
DOI: 10.1002/anie.201706532
Rights: © 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim / This is the accepted version of the following article: Angewandte Chemie - International Edition, 56(39), pp.11855-11859; 2017, which has been published in final form at http://dx.doi.org/10.1002/anie.201706532 This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy http://olabout.wiley.com/WileyCDA/Section/id-820227.html
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/37836

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