Enantioselective Synthesis of (+)-Auriculatol A
A total synthesis of the grayanane diterpenoid (+)-auriculatol A is reported. The synthesis features a convergent coupling strategy that joins two fragments by a vinylogous Mukaiyama-aldol-type reaction and then constructs the 7-membered ring by a Ni-catalyzed enolate alkenylation. Key findings include the development of a chemoselective Ni-catalyzed intramolecular 1,2-addition to access the bicyclo[3.2.1]octane fragment and the use of electron-deficient olefin supporting ligands as uniquely effective for the Ni-catalyzed enolate alkenylation.
Authors
- Conner M. Farley (ORCID: https://orcid.org/0000-0002-4067-0848)
- Jordan K. Thompson (ORCID: https://orcid.org/0009-0007-6395-7087)
- Sarah E. Reisman (ORCID: https://orcid.org/0000-0001-8244-9300)
- Kala C. Youngblood
- Scott C. Virgil (ORCID: https://orcid.org/0000-0001-8586-5641)
- Z. W. Zhang (ORCID: https://orcid.org/0009-0008-7893-1274)
- Yun Hao Shawn Teh (ORCID: https://orcid.org/0009-0005-4981-7841)
Institutions
- California Institute of Technology (US)
- Institute of Chemistry (CN)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2025-11-04
- DOI
- https://doi.org/10.1021/jacs.5c17269
- Citations
- 1
- Primary Topic
- Bioactive Natural Diterpenoids Research
- Type
- article
- Field-Weighted Citation Impact
- 0.81