Scalable Protecting-Group-Free Total Synthesis of Resibufogenin and Bufalin
A chemoenzymatic synthesis access to resibufogenin and bufalin was developed in seven steps without protecting groups. Starting with androstenedione (AD), an α-OH was introduced directly at C14 by hydroxylase P-450<sub>lun</sub>, which was further used as the directing group for hydrogenation to fully control the C17 configuration in the β-orientation after Suzuki cross-coupling. Dehydration of 14α-OH followed by an epoxidation delivered resibufogenin. Simultaneously, bufalin was also obtained via a challenging anaerobic Mukaiyama hydration.
Authors
- Wenbo Ye (ORCID: https://orcid.org/0000-0001-5982-2349)
- Xueqing Zhong
- G. Chen
- Jiange Zhang (ORCID: https://orcid.org/0000-0002-1434-6040)
- Qunfei Zhao (ORCID: https://orcid.org/0000-0003-3115-7337)
- Jun Zhuang (ORCID: https://orcid.org/0000-0002-1815-8653)
- Qiuxin Zhang
- Shao‐Peng Yu
- Rui Zhang (ORCID: https://orcid.org/0000-0003-1370-8289)
- Wenqing Shi
- Fangjie Jin
- Guo‐Qiang Lin (ORCID: https://orcid.org/0000-0002-8209-5263)
- Chao Wang (ORCID: https://orcid.org/0000-0002-3243-3244)
Institutions
- Shanghai University of Traditional Chinese Medicine (CN)
- Shanghai Institute of Organic Chemistry (CN)
- University of Chinese Academy of Sciences (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2024-11-04
- DOI
- https://doi.org/10.1021/acs.orglett.4c03433
- Citations
- 6
- Primary Topic
- Phytochemistry and Bioactive Compounds
- Type
- article
- Field-Weighted Citation Impact
- 1.04
Funders
- Shanghai Municipal Health Commission
- National Natural Science Foundation of China
- Beijing Municipal Administration of Traditional Chinese Medicine