Total Synthesis of (−)‐Perezoperezone through an Intermolecular [5+2] Homodimerization of Hydroxy p‐Quinone

The first copper‐catalyzed intermolecular [5+2] homodimerization of hydroxy p‐quinone is presented, furnishing bicyclo[3.2.1]octadienone core structures in typically good yields and excellent diastereoselectivities. Applying this synthetic approach enables a concise nine‐step total synthesis of (−)‐...

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Published inAngewandte Chemie Vol. 131; no. 49; pp. 17716 - 17721
Main Authors Long, Yang, Ding, Yiming, Wu, Hai, Qu, Chunlei, Liang, Hong, Zhang, Min, Zhao, Xiaoli, Long, Xianwen, Wang, Shu, Puno, Pema‐Tenzin, Deng, Jun
Format Journal Article
LanguageEnglish
Published Weinheim Wiley Subscription Services, Inc 02.12.2019
Subjects
5+2-Cycloaddition
Chemistry
Dimerisierung
Naturstoffe
Perezoperezon
Quinones
Synthesis
Totalsynthese
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Summary:The first copper‐catalyzed intermolecular [5+2] homodimerization of hydroxy p‐quinone is presented, furnishing bicyclo[3.2.1]octadienone core structures in typically good yields and excellent diastereoselectivities. Applying this synthetic approach enables a concise nine‐step total synthesis of (−)‐perezoperezone from commercially available 3,5‐dimethoxytoluene. In neun Schritten: Die erste kupferkatalysierte intermolekulare [5+2]‐Homodimerisierung von Hydroxy‐p‐chinon liefert Bicyclo[3.2.1]octadienon‐Strukturmotive in guten Ausbeuten und exzellenten Diastereoselektivitäten. Die Anwendung dieser Methode ermöglicht die neunstufige Totalsynthese von (−)‐Perezoperezon aus kommerziell erhältlichem 3,5‐Dimethoxytoluol.
Bibliography:These authors contributed equally to this work.
Dedicated to Professor Handong Sun on the occasion of his 80th birthday
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201911978