Work

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

Year: 2024

Type: article

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 five steps.

Source: Nature Communications

DOI: 10.1038/s41467-024-54117-0

Authors: Zhezhe Xu, Weibo Peng, Jiarui Huang, Jinhui Shen, Jing-Jing Guo, Anhua Hu

Institutions: State Key Laboratory of Applied Organic Chemistry, Lanzhou University

Language: English

Topic: Radical Photochemical Reactions

Subfield: Organic Chemistry

Field: Chemistry

Domain: Physical Sciences

Open Access status: gold

Estimated APC paid: $6,790

Funders: Lanzhou University, National Natural Science Foundation of China, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences