Biomimetic Synthesis of Azorellolide via Cyclopropylcarbinyl Cation Chemistry
A concise synthesis of the complex diterpene azorellolide, inspired by speculations on biosynthetic cationic cascades, is presented. The approach, guided by computation, relies on the intramolecular interception of a cyclopropylcarbinyl cation by an appended carboxylate. The successful execution of...
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| Veröffentlicht in: | Journal of the American Chemical Society 2025-01, Vol.147 (1), p.78-83 |
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| container_end_page | 83 |
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| container_issue | 1 |
| container_start_page | 78 |
| container_title | Journal of the American Chemical Society |
| container_volume | 147 |
| creator | Artzy, Jordan Y. Tantillo, Dean J. Trauner, Dirk H. |
| description | A concise synthesis of the complex diterpene azorellolide, inspired by speculations on biosynthetic cationic cascades, is presented. The approach, guided by computation, relies on the intramolecular interception of a cyclopropylcarbinyl cation by an appended carboxylate. The successful execution of this strategy was achieved through acid-catalyzed isomerization of a β-lactone in competition with a type I dyotropic rearrangement. |
| doi_str_mv | 10.1021/jacs.4c14664 |
| format | Article |
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| subjects | Communication |
| title | Biomimetic Synthesis of Azorellolide via Cyclopropylcarbinyl Cation Chemistry |
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