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 this strategy was achieved through acid-catalyzed isomerization of a β-lactone in competition with a type I dyotropic rearrangement.
Authors
- Dirk H. Trauner (ORCID: https://orcid.org/0000-0002-6782-6056)
- Dean J. Tantillo (ORCID: https://orcid.org/0000-0002-2992-8844)
- Jordan Y. Artzy
Institutions
- University of Pennsylvania (US)
- University of California, Davis (US)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2024-12-18
- DOI
- https://doi.org/10.1021/jacs.4c14664
- Citations
- 12
- Primary Topic
- Synthetic Organic Chemistry Methods
- Type
- article
- Field-Weighted Citation Impact
- 3.00
Funders
- National Science Foundation
- University of Pennsylvania
- Directorate for Engineering
- Division of Chemistry