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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Electrochemically Driven Dearomative Spirocyclization of Anisole-Based Cyclopropanols: Total Synthesis of
Shuai Lei1, Zhaojun Ding2, Yankun Zhao1
1Chongqing Key Laboratory of Natural Product Synthesis and Drug Research, Innovative Drug Research Center, School of Pharmaceutical Sciences, Chongqing University, Chongqing 401331, China.
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.
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