Electrochemically Driven Dearomative Spirocyclization of Anisole-Based Cyclopropanols: Total Synthesis of Anhydro-β-rotunol
An eco-friendly electrochemical oxidative dearomatization of anisole-based cyclopropyl alcohols has been developed for synthesizing spiro[4.5]diketones. The reaction involves the simultaneous C-C bond cleavage of cyclopropyl alcohols and spirocyclization with anisole under electrochemical conditions, eliminating the need for metal catalysts or additional oxidants. Via the efficient construction of five- and six-membered rings, this approach enables the synthesis of structurally diverse spirocyclic diketones with a broad substrate scope and compatibility with various functional groups. Notably, the method has been applied to the synthesis of anhydro-β-rotunol, a compound isolated from infected potato tubers and tobacco leaves.
Authors
- Jiayu Mo (ORCID: https://orcid.org/0009-0005-8613-6711)
- Changhong Xie (ORCID: https://orcid.org/0000-0002-2213-5702)
- Chenyang Wang (ORCID: https://orcid.org/0000-0001-6210-4129)
- Zhaojun Ding (ORCID: https://orcid.org/0000-0003-0218-5136)
- Shuai Lei
- Min Zhang (ORCID: https://orcid.org/0000-0002-3851-7836)
- Yankun Zhao
Institutions
- Chongqing University (CN)
- Guangxi Medical University (CN)
- Laboratoire de Chémo-biologie synthétique et thérapeutique (FR)
- First People's Hospital of Chongqing (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-07-16
- DOI
- https://doi.org/10.1021/acs.orglett.5c02177
- Citations
- 1
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China
- Chongqing Science and Technology Commission
- Fundamental Research Funds for the Central Universities
- Chongqing Municipality Key Research and Development Program of China