Electrochemically Driven Dearomative Spirocyclization of Anisole-Based Cyclopropanols: Total Synthesis of Anhydro-β-rotunol

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Abstract
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.
Funding Information
  • Chongqing Municipal Key Research and Development Program of China (CSTB2022TIAD-STX0015)
  • Chongqing Municipal Science and Technology Bureau (CSTB2022NSCQ-LZX0036, CSTB2022NSCQ-MSX0319, CSTB2024YCJH-KYXM0045)
  • Fundamental Research Funds for the Central Universities (2022CDJQY-001, 2024CDJXY002, 2024CDJYXTD-006)
  • National Natural Science Foundation of China (22271033)

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