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

IF 5 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Letters Pub Date : 2025-07-16 DOI:10.1021/acs.orglett.5c02177

Shuai Lei,Zhaojun Ding,Yankun Zhao,Changhong Xie,Chenyang Wang,Jiayu Mo,Min Zhang

引用次数: 0

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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苯环醇基环丙醇的电化学脱芳螺旋环化反应：无水β-罗陀醇的全合成。

以苯甲醚基环丙醇为原料，开发了一种生态友好的电化学氧化脱芳方法，用于合成螺[4.5]二酮。该反应包括在电化学条件下环丙醇的C-C键同时断裂和与苯甲醚的螺环化，不需要金属催化剂或额外的氧化剂。通过高效构建五元环和六元环，该方法可以合成结构多样的螺环二酮，具有广泛的底物范围和与各种官能团的相容性。值得注意的是，该方法已被应用于合成无水β-rotunol，一种从受感染的马铃薯块茎和烟叶中分离出来的化合物。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Organic Letters 化学-有机化学

CiteScore

9.30

自引率

11.50%

发文量

1607

审稿时长

1.5 months

期刊介绍： Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.