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Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability
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| Zeitschriftentitel: | Chemistry – A European Journal |
|---|---|
| Personen und Körperschaften: | , , , , |
| In: | Chemistry – A European Journal, 21, 2015, 41, S. 14507-14518 |
| Format: | E-Article |
| Sprache: | Englisch |
| veröffentlicht: |
Wiley
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| Schlagwörter: |
| author_facet |
Hemberger, Yasmin Zhang, Guoliang Brun, Reto Kaiser, Marcel Bringmann, Gerhard Hemberger, Yasmin Zhang, Guoliang Brun, Reto Kaiser, Marcel Bringmann, Gerhard |
|---|---|
| author |
Hemberger, Yasmin Zhang, Guoliang Brun, Reto Kaiser, Marcel Bringmann, Gerhard |
| spellingShingle |
Hemberger, Yasmin Zhang, Guoliang Brun, Reto Kaiser, Marcel Bringmann, Gerhard Chemistry – A European Journal Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability General Chemistry Catalysis Organic Chemistry |
| author_sort |
hemberger, yasmin |
| spelling |
Hemberger, Yasmin Zhang, Guoliang Brun, Reto Kaiser, Marcel Bringmann, Gerhard 0947-6539 1521-3765 Wiley General Chemistry Catalysis Organic Chemistry http://dx.doi.org/10.1002/chem.201501657 <jats:title>Abstract</jats:title><jats:p>Four new compounds, the monomeric dioncotetralones A (<jats:bold>6 a</jats:bold>) and B (<jats:bold>6 b</jats:bold>) and the dimeric compounds jozimine A<jats:sub>3</jats:sub> (<jats:bold>7</jats:bold>) and jozimine A<jats:sub>4</jats:sub> (<jats:bold>9</jats:bold>), were semi‐synthesized from the natural product dioncophylline A (<jats:bold>4</jats:bold>) and its 5′‐<jats:italic>O</jats:italic>‐demethylated derivative (<jats:bold>5</jats:bold>), respectively, under phenol oxidative reaction conditions. Dioncotetralones A (<jats:bold>6 a</jats:bold>) and B (<jats:bold>6 b</jats:bold>) possess an unprecedented <jats:italic>Z</jats:italic>‐configured double bond, in contrast to the classic biaryl axis that is present in the precursor dioncophylline A (<jats:bold>4</jats:bold>), and an additional stereogenic center at the C2′ atom was generated due to the dearomatization. The resulting steric repulsion forced the expected planar double bond into a helical distorted conformation. The homocoupling of <jats:bold>5</jats:bold> yielded compounds <jats:bold>7</jats:bold> and <jats:bold>9</jats:bold>, the latter of which is the first sp<jats:sup>3</jats:sup>–sp<jats:sup>2</jats:sup> coupled product of a monomeric naphthylisoquinoline with a reduced one and, thus, contains a newly generated stereogenic center. The full stereostructures of <jats:bold>6 a</jats:bold>, <jats:bold>6 b</jats:bold>, <jats:bold>7</jats:bold>, and <jats:bold>9</jats:bold> were successfully elucidated by the interplay of spectroscopic methods (1D/2D NMR and electronic circular‐dichroism spectroscopy) in combination with quantum‐chemical calculations. In addition, compounds <jats:bold>6 a</jats:bold> and <jats:bold>7</jats:bold> exhibited high antiplasmodial activities with excellent half‐maximal inhibitory concentration values.</jats:p> Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability Chemistry – A European Journal |
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Wiley, 2015 |
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Chemistry – A European Journal |
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| title |
Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| title_unstemmed |
Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| title_full |
Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| title_fullStr |
Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| title_full_unstemmed |
Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| title_short |
Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| title_sort |
highly antiplasmodial non‐natural oxidative products of dioncophylline a: synthesis, absolute configuration, and conformational stability |
| topic |
General Chemistry Catalysis Organic Chemistry |
| url |
http://dx.doi.org/10.1002/chem.201501657 |
| publishDate |
2015 |
| physical |
14507-14518 |
| description |
<jats:title>Abstract</jats:title><jats:p>Four new compounds, the monomeric dioncotetralones A (<jats:bold>6 a</jats:bold>) and B (<jats:bold>6 b</jats:bold>) and the dimeric compounds jozimine A<jats:sub>3</jats:sub> (<jats:bold>7</jats:bold>) and jozimine A<jats:sub>4</jats:sub> (<jats:bold>9</jats:bold>), were semi‐synthesized from the natural product dioncophylline A (<jats:bold>4</jats:bold>) and its 5′‐<jats:italic>O</jats:italic>‐demethylated derivative (<jats:bold>5</jats:bold>), respectively, under phenol oxidative reaction conditions. Dioncotetralones A (<jats:bold>6 a</jats:bold>) and B (<jats:bold>6 b</jats:bold>) possess an unprecedented <jats:italic>Z</jats:italic>‐configured double bond, in contrast to the classic biaryl axis that is present in the precursor dioncophylline A (<jats:bold>4</jats:bold>), and an additional stereogenic center at the C2′ atom was generated due to the dearomatization. The resulting steric repulsion forced the expected planar double bond into a helical distorted conformation. The homocoupling of <jats:bold>5</jats:bold> yielded compounds <jats:bold>7</jats:bold> and <jats:bold>9</jats:bold>, the latter of which is the first sp<jats:sup>3</jats:sup>–sp<jats:sup>2</jats:sup> coupled product of a monomeric naphthylisoquinoline with a reduced one and, thus, contains a newly generated stereogenic center. The full stereostructures of <jats:bold>6 a</jats:bold>, <jats:bold>6 b</jats:bold>, <jats:bold>7</jats:bold>, and <jats:bold>9</jats:bold> were successfully elucidated by the interplay of spectroscopic methods (1D/2D NMR and electronic circular‐dichroism spectroscopy) in combination with quantum‐chemical calculations. In addition, compounds <jats:bold>6 a</jats:bold> and <jats:bold>7</jats:bold> exhibited high antiplasmodial activities with excellent half‐maximal inhibitory concentration values.</jats:p> |
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| author | Hemberger, Yasmin, Zhang, Guoliang, Brun, Reto, Kaiser, Marcel, Bringmann, Gerhard |
| author_facet | Hemberger, Yasmin, Zhang, Guoliang, Brun, Reto, Kaiser, Marcel, Bringmann, Gerhard, Hemberger, Yasmin, Zhang, Guoliang, Brun, Reto, Kaiser, Marcel, Bringmann, Gerhard |
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| description | <jats:title>Abstract</jats:title><jats:p>Four new compounds, the monomeric dioncotetralones A (<jats:bold>6 a</jats:bold>) and B (<jats:bold>6 b</jats:bold>) and the dimeric compounds jozimine A<jats:sub>3</jats:sub> (<jats:bold>7</jats:bold>) and jozimine A<jats:sub>4</jats:sub> (<jats:bold>9</jats:bold>), were semi‐synthesized from the natural product dioncophylline A (<jats:bold>4</jats:bold>) and its 5′‐<jats:italic>O</jats:italic>‐demethylated derivative (<jats:bold>5</jats:bold>), respectively, under phenol oxidative reaction conditions. Dioncotetralones A (<jats:bold>6 a</jats:bold>) and B (<jats:bold>6 b</jats:bold>) possess an unprecedented <jats:italic>Z</jats:italic>‐configured double bond, in contrast to the classic biaryl axis that is present in the precursor dioncophylline A (<jats:bold>4</jats:bold>), and an additional stereogenic center at the C2′ atom was generated due to the dearomatization. The resulting steric repulsion forced the expected planar double bond into a helical distorted conformation. The homocoupling of <jats:bold>5</jats:bold> yielded compounds <jats:bold>7</jats:bold> and <jats:bold>9</jats:bold>, the latter of which is the first sp<jats:sup>3</jats:sup>–sp<jats:sup>2</jats:sup> coupled product of a monomeric naphthylisoquinoline with a reduced one and, thus, contains a newly generated stereogenic center. The full stereostructures of <jats:bold>6 a</jats:bold>, <jats:bold>6 b</jats:bold>, <jats:bold>7</jats:bold>, and <jats:bold>9</jats:bold> were successfully elucidated by the interplay of spectroscopic methods (1D/2D NMR and electronic circular‐dichroism spectroscopy) in combination with quantum‐chemical calculations. In addition, compounds <jats:bold>6 a</jats:bold> and <jats:bold>7</jats:bold> exhibited high antiplasmodial activities with excellent half‐maximal inhibitory concentration values.</jats:p> |
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| imprint | Wiley, 2015 |
| imprint_str_mv | Wiley, 2015 |
| institution | DE-D275, DE-Bn3, DE-Brt1, DE-D161, DE-Gla1, DE-Zi4, DE-15, DE-Rs1, DE-Pl11, DE-105, DE-14, DE-Ch1, DE-L229 |
| issn | 0947-6539, 1521-3765 |
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| physical | 14507-14518 |
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| series | Chemistry – A European Journal |
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| spelling | Hemberger, Yasmin Zhang, Guoliang Brun, Reto Kaiser, Marcel Bringmann, Gerhard 0947-6539 1521-3765 Wiley General Chemistry Catalysis Organic Chemistry http://dx.doi.org/10.1002/chem.201501657 <jats:title>Abstract</jats:title><jats:p>Four new compounds, the monomeric dioncotetralones A (<jats:bold>6 a</jats:bold>) and B (<jats:bold>6 b</jats:bold>) and the dimeric compounds jozimine A<jats:sub>3</jats:sub> (<jats:bold>7</jats:bold>) and jozimine A<jats:sub>4</jats:sub> (<jats:bold>9</jats:bold>), were semi‐synthesized from the natural product dioncophylline A (<jats:bold>4</jats:bold>) and its 5′‐<jats:italic>O</jats:italic>‐demethylated derivative (<jats:bold>5</jats:bold>), respectively, under phenol oxidative reaction conditions. Dioncotetralones A (<jats:bold>6 a</jats:bold>) and B (<jats:bold>6 b</jats:bold>) possess an unprecedented <jats:italic>Z</jats:italic>‐configured double bond, in contrast to the classic biaryl axis that is present in the precursor dioncophylline A (<jats:bold>4</jats:bold>), and an additional stereogenic center at the C2′ atom was generated due to the dearomatization. The resulting steric repulsion forced the expected planar double bond into a helical distorted conformation. The homocoupling of <jats:bold>5</jats:bold> yielded compounds <jats:bold>7</jats:bold> and <jats:bold>9</jats:bold>, the latter of which is the first sp<jats:sup>3</jats:sup>–sp<jats:sup>2</jats:sup> coupled product of a monomeric naphthylisoquinoline with a reduced one and, thus, contains a newly generated stereogenic center. The full stereostructures of <jats:bold>6 a</jats:bold>, <jats:bold>6 b</jats:bold>, <jats:bold>7</jats:bold>, and <jats:bold>9</jats:bold> were successfully elucidated by the interplay of spectroscopic methods (1D/2D NMR and electronic circular‐dichroism spectroscopy) in combination with quantum‐chemical calculations. In addition, compounds <jats:bold>6 a</jats:bold> and <jats:bold>7</jats:bold> exhibited high antiplasmodial activities with excellent half‐maximal inhibitory concentration values.</jats:p> Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability Chemistry – A European Journal |
| spellingShingle | Hemberger, Yasmin, Zhang, Guoliang, Brun, Reto, Kaiser, Marcel, Bringmann, Gerhard, Chemistry – A European Journal, Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability, General Chemistry, Catalysis, Organic Chemistry |
| title | Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| title_full | Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| title_fullStr | Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| title_full_unstemmed | Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| title_short | Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| title_sort | highly antiplasmodial non‐natural oxidative products of dioncophylline a: synthesis, absolute configuration, and conformational stability |
| title_unstemmed | Highly Antiplasmodial Non‐Natural Oxidative Products of Dioncophylline A: Synthesis, Absolute Configuration, and Conformational Stability |
| topic | General Chemistry, Catalysis, Organic Chemistry |
| url | http://dx.doi.org/10.1002/chem.201501657 |