A Practical Approach to Cyclopropanation of Masked o‐Benzoquinones with Applications in Tropolone Derivative Synthesis
Year: 2024
Type: article
Abstract: The Corey–Chaykovsky cyclopropanation of readily available masked o‐benzoquinones (MOBs) has been investigated to generate functionalized bicyclo[4.1.0]heptane derivatives with regioselectivity. The resulting bicyclic products were subjected to a sequence of hydrolysis, BF₃ ⋅ Et₂O‐mediated ring‐opening, and then again hydrolysis to access various tropolone derivatives – a class of molecules with significant roles in synthetic, biological, and theoretical chemistry. Utilizing an improved approach based on established cyclopropanation and ring‐opening strategies, several bicyclo[4.1.0]heptanes, tropolone difluorides, and tropolones can be synthesized from readily available MOBs. Our efforts focused on modifying each step to make these reactions general and of considerable practical value.
Authors: Kuan‐Hsun Huang, Yao‐Ping Lo, Anupam Mukherjee, Badugu Devendar, Sandeep Sharma, I.‐Chen Chiu, Yu‐Pei Chang, Yi‐Chuan Chang, Chi‐Phi Wu, Chun‐Chen Liao, Gary Jing Chuang
Language: English
Subfield: Organic Chemistry
Field: Chemistry
Domain: Physical Sciences
Open Access status: bronze
Awards: G1597469621, G6987901003
OpenAlex ID: W4405720159