Photoinduced formal [4 + 2] cycloaddition of two electron-deficient olefins and its application to the synthesis of lucidumone

Zhezhe Xu, Weibo Peng, Jiarui Huang, Jinhui Shen, Jing-Jing Guo () and Anhua Hu ()
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Zhezhe Xu: Lanzhou University
Weibo Peng: Lanzhou University
Jiarui Huang: Lanzhou University
Jinhui Shen: Lanzhou University
Jing-Jing Guo: Lanzhou University
Anhua Hu: Lanzhou University

Nature Communications, 2024, vol. 15, issue 1, 1-7

Abstract: Abstract Electronically mismatched Diels−Alder reaction between two electron-deficient components is synthetically useful and yet underdeveloped under thermal conditions. Herein, a photoinduced formal [4 + 2] cycloaddition of enone with a variety of electron-deficient dienes is described. Key to the success of this stepwise methodology relies on a C − C bond cleavage/rearrangement of the cyclobutane based overbred intermediate via diversified mechanistic pathways. Based on this annulation method, total synthesis of lucidumone is achieved in nine steps.

Date: 2024
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DOI: 10.1038/s41467-024-54117-0

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