Bioinspired Stereoselective Total Synthesis of the Caged Sesquiterpenoid Daphnepapytone A
The first total synthesis of the novel caged sesquiterpenoid daphnepapytone A is disclosed. Key reactions include a Pauson-Khand cycloaddition to provide oleodaphone, a bioinspired photoinduced [2 + 2] cycloaddition to forge the cyclobutane-containing caged skeleton, and a C-H oxidation and reduction protocol to generate daphnepapytone A. Finally, the 17-step synthetic sequence is shortened to 4 steps in protecting group-free and exclusively stereoselective fashion.
Authors
- Xingang Xie (ORCID: https://orcid.org/0000-0002-0707-1229)
- ZhongXiang Zhang (ORCID: https://orcid.org/0000-0003-3479-8666)
- Wei Chen (ORCID: https://orcid.org/0000-0002-8955-9497)
- Kai Liu (ORCID: https://orcid.org/0000-0003-0878-5191)
- Pengfei Yu (ORCID: https://orcid.org/0009-0001-4331-5403)
- Huilin Li (ORCID: https://orcid.org/0000-0001-8088-6718)
- Jia Li (ORCID: https://orcid.org/0000-0002-3148-6897)
- Xuegong She (ORCID: https://orcid.org/0000-0002-3002-2433)
Institutions
- Guizhou University (CN)
- Shanghai Pesticide Research Institute (CN)
- Lanzhou University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-05-15
- DOI
- https://doi.org/10.1021/acs.orglett.5c01509
- Citations
- 6
- Primary Topic
- Chemical synthesis and alkaloids
- Type
- article
- Field-Weighted Citation Impact
- 5.62
Funders
- National Natural Science Foundation of China
- Guizhou University
- Science and Technology Department of Gansu Province