Asymmetric total synthesis of penicilfuranone A through an NHC-catalyzed umpolung strategy
The first asymmetric total synthesis of penicifuranone A was accomplished in eight steps through an NHC-catalyzed umpolung strategy. Key features of the synthesis include an Al-Salen catalyzed asymmetric cyanosilylation to install the tertiary alcohol of gregatin A, and an NHC catalyzed Stetter-Aldol cascade reaction. The umpolung strategy of the benzyl aldehyde fragment facilitated a convergent formal [4 + 2] annulation with gregatin A, ultimately leading to the formation of penicifuranone A.
Authors
- Xianwen Long (ORCID: https://orcid.org/0000-0002-7286-1542)
- Yiming Ding (ORCID: https://orcid.org/0000-0002-1138-8990)
- Jun Deng (ORCID: https://orcid.org/0000-0002-7463-1329)
- Peng George Wang (ORCID: https://orcid.org/0000-0003-3335-6794)
- Pema‐Tenzin Puno (ORCID: https://orcid.org/0000-0001-5212-3000)
- Chunlei Qu
- Xiaodong Yang (ORCID: https://orcid.org/0000-0002-8466-5418)
- Jingwei Zhang (ORCID: https://orcid.org/0000-0002-7882-1832)
Institutions
- Kunming Institute of Botany (CN)
- Yunnan University (CN)
- Nankai University (CN)
Publication Details
- Journal
- Chemical Science
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5sc01508a
- Citations
- 7
- Primary Topic
- Synthesis of Organic Compounds
- Type
- article
- Field-Weighted Citation Impact
- 9.76
Funders
- National Natural Science Foundation of China
- China Postdoctoral Science Foundation
- Nankai University
- Fundamental Research Funds for the Central Universities