基于氧化[3+2]环加成反应合成二氢苯并呋喃类天然产物

doi:10.6023/cjoc202103048

摘要/Abstract

二氢苯并呋喃结构单元广泛存在于生物碱及萜类等多种天然产物中, 这些天然产物大多具有良好的生物活性和药用价值. 因此, 近年来有关具有二氢苯并呋喃环骨架的天然产物全合成工作不断涌现. 综述了近十多年来氧化[3+2]环加成反应在构建二氢苯并呋喃环骨架及各类天然产物全合成方面的应用进展.

关键词: 氧化[3+2]环加成, 二氢苯并呋喃, 天然产物, 全合成, 仿生合成

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

引用此文

赵军, 肖检, 王雅雯, 彭羽. 基于氧化[3+2]环加成反应合成二氢苯并呋喃类天然产物[J]. 有机化学, 2021, 41(8): 2933-2945.

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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图/表 26

图1. 含苯并呋喃骨架的天然产物列举

Figure 1. Natural products with dihydrobenzofuran skeleton

图式1. 呋喃环单元的构建方法列举

Scheme 1. Methods for construction of dihydrobenzofuran

图式2. 三价碘参与的氧化[3+2]环加成反应的机理

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

图式3. Harran小组对(–)-Diazonamide A的全合成

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

图式4. 姚祝军小组对(–)-Azonazine的全合成

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

图式5. Vincent小组对Phalarine骨架的合成研究

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

图式6. 贾彦兴小组对Phalarine的全合成

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

图式7. Nicolaou小组对Haplophytine的全合成

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

图式8. 李超忠小组对(+)-Decursivine的全合成

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

图式9. 夏成峰小组对(+)-Decursivine的全合成

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

图式10. 夏成峰小组对(±)-Serotobenine的全合成

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

图式11. Trauner小组对(±)-Merochlorin B的全合成

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

图式12. 李闯创小组对Hypocrolide A的全合成

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

图式13. 谢志翔小组对Callistrilones A~E的合成

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

图式14. Dethe小组对Viminalins A、B、H和I的合成

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

图式15. Sako小组对Resveratrol和ε-Viniferin二聚体的全合成

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

图式16. Antus小组对Franasols A~C和Dehydrodiisoeugenol的全合成

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

图式17. 王英基小组对(±)-Licarin A和(±)-Acuminatin的合成

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

图式18. Yoon小组对新木脂素类天然产物的合成

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

图式19. 刘强小组对Resveratrol二聚体的合成

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

图式20. 汪义丰小组对3',4-di-O-methylcedrusin的合成

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

图式21. Rindone小组对脱氢双松柏醇的全合成

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

图式22. 涂永强小组对Corsifurans A和B的合成

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

图式23. Morrow 小组对5-carbapterocarpan和紫檀烷的合成

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

图式24. Pappo小组对2'''-dehydroxycalodenin B的合成

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

图式25. 应用氧化[3+2]环加成反应合成天然产物一览

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

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