Asymmetric Total synthesis of Asperones A and B through Organocatalyzed Quinone [5 + 2] Cycloaddition
The first asymmetric total synthesis of the anti-inflammatory polyketides asperones A (<b>1</b>) and B (<b>2</b>) has been accomplished. Key synthetic steps include a Diels-Alder and retro-Diels-Alder cascade to construct the poly substituted phenol, an Al-Salen-catalyzed asymmetric cyanosilylation to form the tertiary alcohol of gregatin A, and an organocatalyzed intermolecular [5 + 2] cycloaddition of <i>p</i>-quinone with electron-deficient alkenes to build the crucial [3.2.1] octane core of asperones A (<b>1</b>) and B (<b>2</b>).
Authors
- Xianwen Long (ORCID: https://orcid.org/0000-0002-7286-1542)
- Yaqiu Zhao
- Yiming Ding (ORCID: https://orcid.org/0000-0002-1138-8990)
- Jun Deng (ORCID: https://orcid.org/0000-0002-7463-1329)
- Lu Chen (ORCID: https://orcid.org/0000-0002-0551-4751)
- Chunlei Qu
- Peng Wang (ORCID: https://orcid.org/0000-0003-0788-6687)
- Jingwei Zhang (ORCID: https://orcid.org/0000-0002-2261-7605)
- Tingrong Zhang (ORCID: https://orcid.org/0000-0003-4500-5297)
Institutions
- Chinese Academy of Medical Sciences & Peking Union Medical College (CN)
- Nankai University (CN)
- China Academy of Chinese Medical Sciences (CN)
Publication Details
- Journal
- Journal of the American Chemical Society
- Published
- 2025-02-13
- DOI
- https://doi.org/10.1021/jacs.4c16252
- Citations
- 12
- Primary Topic
- Microbial Natural Products and Biosynthesis
- Type
- article
- Field-Weighted Citation Impact
- 16.73
Funders
- National Natural Science Foundation of China
- China Postdoctoral Science Foundation
- Fundamental Research Funds for the Central Universities