Advances on the Synthesis of Natural Products with Dihydrobenzofuran Skeleton via Oxidative [3+2] Cycloadditions

doi:10.6023/cjoc202103048

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 2933-2945.DOI: 10.6023/cjoc202103048 Previous Articles Next Articles

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基于氧化[3+2]环加成反应合成二氢苯并呋喃类天然产物

赵军^a, 肖检^a^,^*(), 王雅雯^a, 彭羽^a^,^b^,^*()

a 西南交通大学生命科学与工程学院四川省天然药物仿生合成工程研究中心成都 610031
b 伊犁师范大学化学与环境科学学院新疆伊宁 835000

收稿日期:2021-03-26 修回日期:2021-04-21 发布日期:2021-05-14
通讯作者: 肖检, 彭羽
基金资助:
国家自然科学基金(21772078); 国家自然科学基金(22071200); 四川省科技计划(2020JDRC0021); 中央高校基本科研业务费专项资金(2682020CX55)

Advances on the Synthesis of Natural Products with Dihydrobenzofuran Skeleton via Oxidative [3+2] Cycloadditions

Jun Zhao^a, Jian Xiao^a(), Yawen Wang^a, Yu Peng^a^,^b()

a Engineering Research Center of Biomimetic Synthesis of Natural Drugs of Sichuan Province, School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031
b School of Chemistry and Environment Science, Yili Normal University, Yining, Xinjiang 835000

Received:2021-03-26 Revised:2021-04-21 Published:2021-05-14
Contact: Jian Xiao, Yu Peng
Supported by:
National Natural Science Foundation of China(21772078); National Natural Science Foundation of China(22071200); Science and Technology Department of Sichuan Province(2020JDRC0021); Fundamental Research Funds for the Central Universities(2682020CX55)

Dihydrobenzofuran structure units widely exist in a variety of natural products, such as alkaloids and terpenes. The total synthesis of natural products containing dihydrobenzofuran skeleton has thus emerged in recent years, because of their good biological activities and medicinal value. The application progress of oxidative [3+2] cycloaddition in the construction of dihydrobenzofuran ring skeleton and the total synthesis of various natural products in recent ten years was reviewed.

Key words: oxidative [3+2] cycloaddition, dihydrobenzofuran, natural product, total synthesis, biomimetic synthesis

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Jun Zhao, Jian Xiao, Yawen Wang, Yu Peng. Advances on the Synthesis of Natural Products with Dihydrobenzofuran Skeleton via Oxidative [3+2] Cycloadditions[J]. Chinese Journal of Organic Chemistry, 2021, 41(8): 2933-2945.

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Fig. & Tab. 26

Figure 1. Natural products with dihydrobenzofuran skeleton

Scheme 1. Methods for construction of dihydrobenzofuran

Scheme 2. Mechanism of oxidative [3+2] cycloaddition reaction with trivalent iodine

Scheme 3. Total synthesis of (–)-Diazonamide A by Harran’s group

Scheme 4. Total synthesis of (–)-Azonazine by Yao’s group

Scheme 5. Synthetic studies of Phalarine skeleton by Vincent’s group

Scheme 6. Total synthesis of Phalarine by Jia’s group

Scheme 7. Total synthesis of Haplophytine by Nicolaou’s group

Scheme 8. Total synthesis of (+)-Decursivine by Li’s group

Scheme 9. Total synthesis of (+)-Decursivine by Xia’s group

Scheme 10. Total synthesis of (±)-Serotobenine by Xia’s group

Scheme 11. Total synthesis of (±)-Merochlorin B by Trauner’s group

Scheme 12. Total synthesis of Hypocrolide A by Li’s group

Scheme 13. Total synthesis of Callistrilones A~E by Xie’s group

Scheme 14. Total synthesis of Viminalins A, B, H and I by Dethe’s group

Scheme 15. Total synthesis of dimer of Resveratrol and ε-Viniferin by Sako’s group

Scheme 16. Total synthesis of Franasols A~C and Dehydrodiisoeugenol by Antus’s group

Scheme 17. Total synthesis of (±)-Licarin A and (±)-Acuminatin by Wang’s group

Scheme 18. Synthesis of new natural products of lignans by Yoon’s group

Scheme 19. Total synthesis of the dimer of Resveratrol by Liu’s group

Scheme 20. Synthesis of 3',4-di-O-methylcedrusin by Wang’s group

Scheme 21. Total synthesis of dehydrobisconiferyl alcohol by Rindone’s group

Scheme 22. Synthesis of Corsifurans A and B by Tu’s group

Scheme 23. Synthesis of 5-carbapterocarpan and pterocarpans by Morrow’s group

Scheme 24. Synthesis of 2'''-dehydroxycalodenin B by Pappo’s group

Scheme 25. Natural products synthesis via oxidative [3+2] cycloaddition

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基于氧化[3+2]环加成反应合成二氢苯并呋喃类天然产物

Advances on the Synthesis of Natural Products with Dihydrobenzofuran Skeleton via Oxidative [3+2] Cycloadditions

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Fig. & Tab. 26

References 29

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