Application of Acyl Radical in Total Synthesis of Natural Products

doi:10.6023/cjoc202409033

Chinese Journal of Organic Chemistry ›› 2025, Vol. 45 ›› Issue (3): 852-861.DOI: 10.6023/cjoc202409033 Previous Articles Next Articles

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酰基自由基化学在天然产物全合成中的应用

谢应^a, 付绍敏^b, 刘波^b^,^*()

a 四川轻化工大学化学与环境工程学院四川自贡 643000
b 四川大学化学学院绿色化学与技术教育部重点实验室成都 610064

收稿日期:2024-09-24 修回日期:2024-11-28 发布日期:2024-12-19
基金资助:
国家自然科学基金(21925106); 国家自然科学基金(21921002)

Application of Acyl Radical in Total Synthesis of Natural Products

Ying Xie^a, Shaomin Fu^b, Bo Liu^b()

a School of Chemistry and Environmental Engineering, Sichuan University of Science & Engineering, Zigong, Sichuan 643000
b Key Laboratory of Green Chemistry & Technology of Ministry of Education, College of Chemistry, Sichuan University, Chengdu, 610064

Received:2024-09-24 Revised:2024-11-28 Published:2024-12-19
Contact: * E-mail: chembliu@scu.edu.cn
Supported by:
National Natural Science Foundation of China(21925106); National Natural Science Foundation of China(21921002)

Acyl radicals have received extensive attention from organic synthetic chemists due to their unique structural features and high reactivity. In recent years, with the continuous innovation of their acyl sources and initiation modes, acyl radicals have been widely used in various chemical transformations. Especially in the critical step of the late stage of natural product synthesis, acyl radicals have become one of the effective and important strategies compatible with a wide range of functional groups due to the advantages of their smaller site resistance and less susceptibility to metal-mediated β-elimination reactions. Application of acyl radicals as a key step in the synthesis of natural products is summarized.

Key words: acyl radicals, natural products, total synthesis, radical cyclization

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Ying Xie, Shaomin Fu, Bo Liu. Application of Acyl Radical in Total Synthesis of Natural Products[J]. Chinese Journal of Organic Chemistry, 2025, 45(3): 852-861.

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Fig. & Tab. 22

Scheme 1. Application of acyl radicals in the synthesis of natural products

Scheme 2. Total synthesis of coniine

Scheme 3. Total synthesis of hinokinin and dihydrocapsaicin

Scheme 4. Total synthesis of roseophilin

Scheme 5. Construction of the himbacine core skeleto

Scheme 6. Total synthesis of guatambuine

Scheme 7. Total synthesis of calothrixin B

Scheme 8. Acyl radical cyclization constructs the core backbone of uleine

Scheme 9. Acyl radical cyclization constructs the core skeleton of actinophyllic acid

Scheme 10. Total synthesis of acanthodoral

Scheme 11. Acyl free construction of polyether natural product fragments

Scheme 12. Total synthesis of strophasterols A and B

Scheme 13. Total synthesis of No. 2106A

Scheme 14. Total synthesis of pinnigorgiols B and E

Scheme 15. Total synthesis of clionastatins A and B

Scheme 16. Total synthesis of allokainic

Scheme 17. Biomimetic syntheses of (±)-isopalhinine A, (±)-palhinines A and D

Scheme 18. Convergent synthesis of cotylenin A

Scheme 19. Total synthesis of brevione C

Scheme 20. Total synthesis of flueggeacosine B

Scheme 21. Construction of bicyclo[2.2.2]octanones by acyl radical cyclization/rearrangement reactions

Scheme 22. Photocatalytic [3+2] cycloaddition of alkyl aldehydes and alkynes

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酰基自由基化学在天然产物全合成中的应用

Application of Acyl Radical in Total Synthesis of Natural Products

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