Total Synthesis of Complex Natural Products Via Radical-Mediated Formal Diels-Alder Reaction

doi:10.6023/A25040131

Acta Chimica Sinica ›› 2025, Vol. 83 ›› Issue (11): 1424-1434.DOI: 10.6023/A25040131 Previous Articles Next Articles

Review

基于自由基介导Formal Diels-Alder反应的复杂天然产物全合成

黄俊^*(), 尹蓉, 曹婷婷

南华大学化学化工学院湖南衡阳 421001

投稿日期:2025-04-24 发布日期:2025-05-22

作者简介:

黄俊, 教授, 博士生导师. 2010年7月毕业于中国农业大学理学院化学系, 获得理学学士学位; 2015年7月于北京大学获得博士学位; 2015年8月至2016年9月于美国纽约州立大学奥尔巴尼分校进行博士后研究; 2016年10月至2021年9月就职于北京大学深圳研究生院; 2021年10月至今, 就职于南华大学化学化工学院. 主要从事天然产物全合成及合成方法学研究.

尹蓉, 2022年7月于湖南理工学院获得理学学士学位, 同年进入南华大学攻读硕士学位. 指导教师为黄俊教授, 研究方向为天然小分子药物全合成. 目前已完成鬼臼毒素类家族分子的结构多样性全合成研究.

曹婷婷, 2017年7月于湖北大学获得理学学士学位; 2022年7月于北京大学获得博士学位; 目前于英国格拉斯哥大学进行博士后研究. 研究方向为人工智能和自动化化学合成.

基金资助:
项目受国家自然科学基金(22371117); 湖南省科技创新计划(2022RC1106)

Total Synthesis of Complex Natural Products Via Radical-Mediated Formal Diels-Alder Reaction

Huang Jun^*(), Yin Rong, Cao Tingting

School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001

Received:2025-04-24 Published:2025-05-22
Contact: *E-mail: junhuang@usc.edu.cn
Supported by:
National Natural Science Foundation of China(22371117); Science and Technology Innovation Program of Hunan Province(2022RC1106)

In recent years, the radical-mediated formal Diels-Alder reaction of dienophiles and dienes under mild conditions has provided a novel approach for the stereoselective construction of six-membered ring skeleton. This review offers a concise overview of the application of radical-mediated formal Diels-Alder reactions in the total synthesis of bioactive complex natural products. It mainly includes three types of reaction pathways: (1) the radical cation-mediated formal Diels-Alder reaction, (2) the single-electron-transfer-initiated formal Diels-Alder reaction, and the diradical-involved formal Diels-Alder reaction, which enable the stereoselective generation of target ring systems.

Key words: radical cation, diradical, formal-Diels-Alder reaction, [4＋2]-cycloaddition reaction, total synthesis of natural products

Cite this article

Huang Jun, Yin Rong, Cao Tingting. Total Synthesis of Complex Natural Products Via Radical-Mediated Formal Diels-Alder Reaction[J]. Acta Chimica Sinica, 2025, 83(11): 1424-1434.

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Fig. & Tab. 12

Scheme 1. Applications of the Diels-Alder reaction in the total synthesis of representative natural products

Scheme 2. Reaction types of radical-meidated formal Diels-Alder reaction: (a) cation radical; (b) single electron transfer (SET); (c) diradical

Scheme 3. Cation radical-mediated formal Diels-Alder reaction

Scheme 4. Total synthesis of (－)-β-Selinene

Scheme 5. Total synthesis of Kingianins A, D and F

Scheme 6. Total synthesis of Kingianin A

Scheme 7. Total synthesis of Brosimones A and B

Scheme 8. Total synthesis of aryltetralin ether lignans

Scheme 9. Proposed biosynthetic pathway of 1,4-benzodioxane lignans

Scheme 10. Total synthesis of (±)-Aiphanol and (±)-nitidanin

Scheme 11. Total synthesis of Brevitaxin

Scheme 12. Total synthesis of Lucidumone

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基于自由基介导Formal Diels-Alder反应的复杂天然产物全合成

Total Synthesis of Complex Natural Products Via Radical-Mediated Formal Diels-Alder Reaction

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