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 in | Angewandte Chemie Vol. 131; no. 49; pp. 17716 - 17721 |
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| Main Authors | , , , , , , , , , , |
| Format | Journal Article |
| Language | English |
| Published |
Weinheim
Wiley Subscription Services, Inc
02.12.2019
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| Abstract | 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. |
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| AbstractList | 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. 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. Abstract 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. |
| Author | Long, Xianwen Liang, Hong Deng, Jun Puno, Pema‐Tenzin Qu, Chunlei Wang, Shu Zhao, Xiaoli Ding, Yiming Wu, Hai Long, Yang Zhang, Min |
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| Notes | These authors contributed equally to this work. Dedicated to Professor Handong Sun on the occasion of his 80th birthday |
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| Snippet | The first copper‐catalyzed intermolecular [5+2] homodimerization of hydroxy p‐quinone is presented, furnishing bicyclo[3.2.1]octadienone core structures in... Abstract The first copper‐catalyzed intermolecular [5+2] homodimerization of hydroxy p ‐quinone is presented, furnishing bicyclo[3.2.1]octadienone core... |
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| SubjectTerms | 5+2-Cycloaddition Chemistry Dimerisierung Naturstoffe Perezoperezon Quinones Synthesis Totalsynthese |
| Title | Total Synthesis of (−)‐Perezoperezone through an Intermolecular [5+2] Homodimerization of Hydroxy p‐Quinone |
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