Mizoroki-Heck反应在天然产物全合成中的应用进展★

doi:10.6023/A26050154

化学学报 ›› 2026, Vol. 84 ›› Issue (6): 933-968.DOI: 10.6023/A26050154 上一篇下一篇

综述

Mizoroki-Heck反应在天然产物全合成中的应用进展^★

张华轩, 刘月, 苏绪娟, 谢新刚^*(), 厍学功

兰州大学化学化工学院天然产物化学全国重点实验室兰州 730000

投稿日期:2026-05-13 发布日期:2026-06-09

作者简介:

张华轩, 男, 本科毕业于西北农林科技大学化学与药学院, 现为兰州大学化学化工学院2023级研究生, 研究方向为: 天然产物全合成.

刘月, 女, 兰州大学化学化工学院2024级研究生, 研究方向为: 天然产物全合成.

苏绪娟, 女, 兰州大学化学化工学院2025级研究生, 研究方向为: 天然产物全合成.

谢新刚, 副教授, 硕士生导师. 2006年6月毕业于兰州大学化学化工学院, 获博士学位. 2006年7月赴香港中文大学化学系, 进行博士后研究. 2010年6月加入兰州大学功能有机分子化学国家重点实验室, 2025年1月改组为天然产物化学全国重点实验室. 课题组主要从事具有良好生理活性的天然产物全合成和绿色、高效的合成方法学研究. 独立工作以来已在Nat. Commun., Org. Lett., Green Chem., Org. Chem. Front.和J. Org. Chem.等国际著名期刊上发表学术论文60余篇.

厍学功, 教授, 博士生导师. 1999年获兰州大学有机化学博士学位, 同年赴美国科罗拉多州立大学和俄勒冈大学从事博士后研究(1999-2002年). 2002年回国后任兰州大学功能有机分子化学国家重点实验室副主任、教授, 博士生导师, 2025年1月改组为天然产物化学全国重点实验室. 课题组主要从事具有良好生理活性的复杂天然产物不对称全合成, 获国家杰出青年科学基金(2011年)、Thieme Chemistry Journal Award(2007年)及甘肃省自然科学一等奖(2015年)等荣誉, 在J. Am. Chem. Soc., Angew. Chem. Int. Ed., Org. Lett.和J. Org. Chem.等期刊发表SCI论文180余篇.

^★“纪念兰州大学化学学科创建80周年”专辑

基金资助:
甘肃省科技重大专项(23ZDFA015); 甘肃省科技重大专项(24ZD13FA017); 深圳市基础研究专项自然科学基金计划面上项目(JCYJ20250604172759009)

Advances in the Application of Mizoroki-Heck Reaction in Natural Product Synthesis^★

Huaxuan Zhang, Yue Liu, Xujuan Su, Xingang Xie^*(), Xuegong She

State Key Laboratory of Natural Product Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, China

Received:2026-05-13 Published:2026-06-09
Contact: *E-mail: xiexg@lzu.edu.cn
About author:
^★For the VSI “Celebration of 80th Anniversary of Chemistry in Lanzhou University”
Supported by:
Major Science and Technology Project of Gansu Province(23ZDFA015); Major Science and Technology Project of Gansu Province(24ZD13FA017); General Program of Shenzhen Basic Research Project (Natural Science Foundation)(JCYJ20250604172759009)

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摘要/Abstract

Mizoroki-Heck偶联反应是重要的钯催化C—C键构建反应, 广泛应用于天然产物全合成. 本文综述2021~2026年初相关研究进展, 按分子间与分子内反应分类, 梳理其在生物碱、萜类、芳香类及聚酮类天然产物合成中的应用. 该反应可高效实现片段偶联与环系构筑, 结合不对称、还原型、插羰及串联策略, 显著缩短合成路线、提升立体选择性与步骤经济性. Heck反应不断与新型催化体系融合, 为复杂活性天然产物的高效制备与药物研发提供关键支撑.

关键词: Mizoroki-Heck反应, 天然产物全合成, 钯催化, 偶联反应, 环化反应

The Mizoroki-Heck coupling reaction serves as one of the most fundamental and powerful palladium-catalyzed organic transformations, which enables the precise and efficient construction of carbon-carbon bonds in complex molecular systems. Benefiting from its excellent substrate compatibility, remarkable functional-group tolerance and reliable reaction efficiency, this reaction has evolved into an indispensable synthetic tool in the field of natural product total synthesis and is widely adopted for the structural modification and skeleton assembly of various complex natural molecules. This article systematically reviews the cutting-edge research progress of Mizoroki-Heck coupling reactions from 2021 to early 2026. Relevant studies are classified into intermolecular and intramolecular Heck reactions according to distinct reaction modes, and we comprehensively summarize their practical applications and unique technical advantages in the total synthesis of a variety of mainstream natural product families, including alkaloids, terpenoids, aromatic compounds, and polyketides. As a robust synthetic strategy, the Mizoroki-Heck reaction is capable of realizing efficient fragment coupling and sophisticated polycyclic skeleton construction, which effectively addresses the core structural assembly challenges encountered in the synthesis of complex natural products. In such synthetic applications, intramolecular Heck reactions are more frequently utilized than intermolecular ones. Nevertheless, precise regulation of regioselectivity and effective stereochemical control remain the central research focuses and major technical challenges restricting the further development of this reaction. Furthermore, the rational combination of traditional Heck coupling with asymmetric catalysis, reductive Heck reactions, carbonylative modification, and cascade reaction strategies can significantly streamline synthetic routes, improve stereoselective control, and greatly enhance the overall step economy of synthetic sequences. In recent years, the continuous integration of Heck reactions with innovative catalytic systems and advanced synthetic methodologies has further broadened its application scope, providing solid support for the efficient preparation of structurally complex, biologically active natural products, synthetic process optimization, and the sustainable development of novel drug research and development.

Key words: Mizoroki-Heck reaction, total synthesis of natural products, palladium catalysis, coupling reaction, cyclization reaction

引用此文

张华轩, 刘月, 苏绪娟, 谢新刚, 厍学功. Mizoroki-Heck反应在天然产物全合成中的应用进展^★[J]. 化学学报, 2026, 84(6): 933-968.

Huaxuan Zhang, Yue Liu, Xujuan Su, Xingang Xie, Xuegong She. Advances in the Application of Mizoroki-Heck Reaction in Natural Product Synthesis^★[J]. Acta Chimica Sinica, 2026, 84(6): 933-968.

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图/表 57

图式1. Mizoroki-Heck反应和还原型Heck反应机理比较

Scheme 1. Mechanistic comparison between classical Mizoroki-Heck reactions and reductive Heck reactions

图式2. 2021年江世智与颜桂炀团队对Indiacen A的全合成

Scheme 2. Jiang and Yan group’s total synthesis of Indiacen A (2021)

图式3. 2024年孙域课题组对(－)-Norzoanthamine的不对称全合成

Scheme 3. Sun group’s asymmetric total synthesis of (－)-Norzoan- thamine (2024)

图式4. 2026年Opatz课题组对(－)-Strychnine的不对称全合成

Scheme 4. Opatz group’s asymmetric total synthesis of (－)-Strychnine (2026)

图式5. 2021年Nakazaki课题组对(＋)-Cannogenol的不对称全合成

Scheme 5. Nakazaki group’s asymmetric total synthesis of (＋)-Cannogenol (2021)

图式6. 2023年Nakazaki课题组对(－)-Picrotoxinin的不对称全合成

Scheme 6. Nakazaki group’s asymmetric total synthesis of (－)-Picrotoxinin (2023)

图式7. 2023年Nakazaki课题组对19-Nordigitoxigenin的不对称全合成

Scheme 7. Nakazaki group’s asymmetric total synthesis of 19-Nordigitoxigenin (2023)

图式8. 2025年桂敬汉课题组对(＋)-Swinhoeisterols A−C的不对称合成

Scheme 8. Gui group’s asymmetric total synthesis of (＋)-Swinhoeisterols A−C (2025)

图式9. 2025年李超课题组对(＋)-Peniciacetal I和(＋)-Berkeleyacetal D的不对称全合成

Scheme 9. Li group’s asymmetric total synthesis of (＋)-Peniciacetal I and (＋)-Berkeleyacetal D (2025)

图式10. 2021年Shin课题组对Resvebassianol A和3-O-β-(4'''-O-methylglucopyranosyl) resveratrol的全合成

Scheme 10. Shin group’s total synthesis of Resvebassianol A and 3-O-β-(4'''-O-methylglucopyranosyl) resveratrol (2021)

图式11. 2021年李剑峰与张荣平团队对Piceatannol-3'-O-β-D-glucopyranoside的全合成

Scheme 11. Li and Zhang group’s total synthesis of Piceatannol-3'-O-β-D-glucopyranoside (2021)

图式12. 2022年雷婷与江世智团队对Murraol与(E)-Suberenol的全合成

Scheme 12. Lei and Jiang group’s total synthesis of Murraol and (E)-Suberenol (2022)

图式13. 2022年Lucero课题组对Lorneic acid A和J的全合成

Scheme 13. Lucero group’s total synthesis of Lorneic acid A and J (2022)

图式14. 2023年Nagamitsu课题组对(＋)-Tanzawaic acid A的不对称全合成

Scheme 14. Nagamitsu group’s asymmetric total synthesis of (＋)-Tanzawaic acid A (2023)

图式15. 2024年Kim与Yoon团队对Cypripedin的全合成

Scheme 15. Kim and Yoon group’s total synthesis of Cypripedinand (2024)

图式16. 2021年Sittihan课题组对Microansamycin I 的全合成

Scheme 16. Sittihan group’s total synthesis of Microansamycin I (2021)

图式17. 2022年Patel、Petrone与Sarlah团队对(＋)-Darobactin A的不对称全合成

Scheme 17. Patel, Petrone and Sarlah group’s asymmetric total synthesis of (＋)-Darobactin A (2022)

图式18. 2025年Goswami课题组对(＋)-Thailandamide A的不对称全合成

Scheme 18. Goswami group’s asymmetric total synthesis of (＋)-Thailandamide A (2025)

图式19. 2021年Watson课题组对Impatien A的全合成

Scheme 19. Watson group’s total synthesis of Impatien A (2021)

图式20. 2021年Konno课题组对Berberine的全合成

Scheme 20. Konno group’s total synthesis of Berberine (2021)

图式21. 2021年张敏课题组对(＋)-Strempeliopine、(＋)-Schizozygine、(＋)-α-Schizozygol和(＋)-3-oxo-14α,15α-epoxy-Schizozygine的不对称全合成

Scheme 21. Zhang group’s asymmetric total synthesis of (＋)-Strempeliopine, (＋)-Schizozygine, (＋)-α-Schizozygol and (＋)-3-oxo-14α,15α-epoxy- Schizozygine (2021)

图式22. 2021年翟宏斌课题组对(－)-Scholarisine C、(－)-Picrinine和(＋)-5-β-Methoxyaspidophylline的不对称全合成

Scheme 22. Zhai group’s asymmetric total synthesis of (－)-Scholarisine C, (－)-Picrinine and (＋)-5-β-Methoxyaspidophylline (2021)

图式23. 2022年厍学功课题组对(＋)-Lycoposerramine Q、(＋)-Fawcettidine、(＋)-Fawcettimine和(－)-Phlegmariurine B的不对称全合成

Scheme 23. She group’s asymmetric total synthesis of (＋)-Lycoposerramine Q, (＋)-Fawcettidine, (＋)-Fawcettimine and (－)-Phlegmariurine B (2022)

图式24. 2022年孙国新与齐湘兵团队对(－)-Dehydrotubifoline、(－)-Tubifoline和(－)-Tubifolidine的不对称全合成

Scheme 24. Sun and Qi group’s asymmetric total synthesis of (－)-Dehydrotubifoline, (－)-Tubifoline and (－)-Tubifolidine (2022)

图式25. 2022年Wipf课题组对Lysergol和Isolysergol的全合成

Scheme 25. Wipf group’s total synthesis of Lysergol and Isolysergol (2022)

图式26. 2022年翟宏斌与吴云东团队对(－)-Arbophyllidine的不对称全合成

Scheme 26. Zhai and Wu group’s asymmetric total synthesis of (－)-Arbophyllidine (2022)

图式27. 2022年童荣标课题组对(＋)-Paspalicine、(＋)-Paspalinine和(－)-Paspalinine-13-ene的不对称全合成

Scheme 27. Tong group’s asymmetric total synthesis of (＋)-Paspalicine, (＋)-Paspalinine and (－)-Paspalinine-13-ene (2022)

图式28. 2023年Newhouse课题组对(＋)-Shearilicine的不对称全合成

Scheme 28. Newhouse group’s asymmetric total synthesis of (＋)-Shearilicine (2023)

图式29. 2023年Hamlin与Dixon团队对(－)-Himalensine A的不对称全合成

Scheme 29. Hamlin and Dixon group’s asymmetric total synthesis of (－)-Himalensine A (2023)

图式30. 2023年翟宏斌课题组对(－)-Daphnezomines A、B和(＋)-Dapholdhamine B的不对称全合成

Scheme 30. Zhai group’s asymmetric total synthesis of (－)-Daphnezomines A, B and (＋)-Dapholdhamine B (2023)

图式31. 2023年翟宏斌与汪太民团队对(＋)-Tubingensin A的不对称全合成

Scheme 31. Zhai and Wang group’s asymmetric total synthesis of (＋)-Tubingensin A (2023)

图式32. 2024年Kwan与Burns团队对(＋)-Discorhabdin V的不对称全合成

Scheme 32. Kwan and Burns group’s asymmetric total synthesis of (＋)-Discorhabdin V (2024)

图式33. 2024年Vyvyan课题组对(＋)-Cananodine的不对称全合成

Scheme 33. Vyvyan group’s asymmetric total synthesis of (＋)-Cananodine (2024)

图式34. 2024年秦勇与刘小宇团队对(－)-Garryine的不对称全合成

Scheme 34. Qin and Liu group’s asymmetric total synthesis of (－)-Garryine (2024)

图式35. 2024年Bisai课题组对(－)-Codeine的不对称全合成

Scheme 35. Bisai group’s asymmetric total synthesis of (－)-Codeine (2024)

图式36. 2024年杨玉荣课题组对(－)-Daphenylline的不对称全合成

Scheme 36. Yang group’s asymmetric total synthesis of (－)-Daphenylline (2024)

图式37. 2024年马志强课题组对(＋)-Alstrostine G的不对称全合成

Scheme 37. Ma group’s asymmetric total synthesis of (＋)-Alstrostine G (2024)

图式38. 2025年Cho课题组对(＋)-19,20-Dehydroervatamine 和(－)-Ervatamine的不对称全合成

Scheme 38. Cho group’s asymmetric total synthesis of (＋)-19,20-Dehydroervatamine and (－)-Ervatamine (2025)

图式39. 2025年赵勤实课题组对(－)-Hupserrine A、(－)-Huperzimine、(－)-Lycoposerramine R和(－)-Carinatine A的不对称全合成

Scheme 39. Zhao group’s asymmetric total synthesis of (－)-Hupserrine A, (－)-Huperzimine, (－)-Lycoposerramine R and (－)-Carinatine A (2025)

图式40. 2026年马爱军、彭金宝与闫加磊团队对(－)-Galanthamine、(－)-Narwedine、(－)-Lycoraminone和(－)-Lycoramine的不对称全合成

Scheme 40. Ma, Peng and Yan group’s asymmetric total synthesis of (－)-Galanthamine, (－)-Narwedine, (－)-Lycoraminone and (－)-Lycoramine (2026)

图式41. 2026年Yokoshima课题组对Scandine的全合成

Scheme 41. Yokoshima group’s total synthesis of Scandine (2026)

图式42. 2021年鲁照永课题组对Dysiherbol A的全合成

Scheme 42. Lu group’s total synthesis of Dysiherbol A (2021)

图式43. 2021年桂敬汉课题组对(＋)-Clionastatin A和B的不对称全合成

Scheme 43. Gui group’s asymmetric total synthesis of (＋)-Clionastatin A and B (2021)

图式44. 2021年秦红波课题组对Dysifragilones A、B和Dysidavarone C的全合成

Scheme 44. Qin group’s total synthesis of Dysifragilones A, B和Dysidavarone C (2021)

图式45. 2021年董广彬课题组对Phainanoid A的全合成

Scheme 45. Dong group’s total synthesis of Phainanoid A (2021)

图式46. 2022年Micalizio课题组对(－)-Octanorcucurbitacin B的不对称全合成

Scheme 46. Micalizio group’s asymmetric total synthesis of (－)-Octanorcucurbitacin B (2022)

图式47. 2023年阳铭课题组对Illisimonin A的全合成

Scheme 47. Yang group’s total synthesis of Illisimonin A (2023)

图式48. 2024年陆钊洪课题组对(－)-Bipolarolide D的不对称全合成

Scheme 48. Lu group’s asymmetric total synthesis of (－)-Bipolarolide D (2024)

图式49. 2025年Newhouse课题组对(＋)-Thaigranatin V、(－)-Thaigranatin P、(＋)-Erythrocarpines M和(－)-Erythrocarpines L的不对称全合成

Scheme 49. Newhouse group’s asymmetric total synthesis of (＋)-Thaigranatin V, (－)-Thaigranatin P, (＋)-Erythrocarpines M and (－)-Erythrocarpines L (2025)

图式50. Sarlah课题组2025年对(＋)-Nimbolide的不对称全合成和2026年对Hypophyllins E和F的不对称全合成

Scheme 50. Sarlah group’s asymmetric total synthesis of (＋)-Nimbolide (2025) and (＋)-Hypophyllins E and F (2026)

图式51. 2025年胡鹏飞课题组对(－)-Glycinoeclepin A的不对称全合成

Scheme 51. Hu group’s asymmetric total synthesis of (－)-Glycinoeclepin A (2025)

图式52. 2026年阳铭课题组对Anisatin、Neoanisatin、Majusanols A和B的全合成

Scheme 52. Yang group’s total synthesis of Anisatin, Neoanisatin, Majusanols A and B (2026)

图式53. 2026年Maimone课题组对(＋)-Mangicol D的不对称全合成

Scheme 53. Maimone group’s asymmetric total synthesis of (＋)-Mangicol D (2026)

图式54. 2021年Kwon课题组对Plakorsins A、B、D和Rosefuran的全合成

Scheme 54. Kwon group’s total synthesis of Plakorsins A, B, D and Rosefuran (2021)

图式55. 2021年Tambar课题组对(＋)-Rubellin C的不对称全合成

Scheme 55. Tambar group’s asymmetric total synthesis of (＋)-Rubellin C (2021)

图式56. 2025年房显赫与毕毅团队对(－)-Steganol、(－)-Steganacin和(－)-Steganone的不对称全合成

Scheme 56. Fang and Bi group’s asymmetric total synthesis of (－)-Steganol, (－)-Steganacin and (－)-Steganone (2025)

图式57. 2022年Bach课题组对Pulvomycin D的不对称全合成

Scheme 57. Bach group’s asymmetric total synthesis of Pulvomycin D (2022)

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Mizoroki-Heck反应在天然产物全合成中的应用进展^★

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