四川大学化学学院
师资力量

刘 波     教授、博士生导师、副院长

研究方向:具有重要生物活性的复杂天然产物全合成;天然产物分子探针的生物学功能开发;合成导向的反应方法学研究

联系方式:028-85413712          Email:chembliu@scu.edu.cn

个人主页:点击进入

简历

1994.9.---1998.7.   在西南师范大学化学化工学院学习,环境学专业;获理学学士学位

1998.9.---2001.7.   在中科院成都有机化学研究所学习,有机合成专业,主要从事不对称催化反应研究;获理学硕士学位;导师:冯小明 研究员;蒋耀忠 研究员

2001.9.---2004.7.   在中科院上海有机化学研究所学习,有机合成专业,主要从事天然产物全合成研究;获理学博士学位;导师:周维善 研究员

2004.9.---2007.3.   在美国德克萨斯大学西南医学中心作博士后研究,主要从事过渡金属催化的反应研究及天然产物全合成;导师:Prof. Jef K. De Brabander

2007.6.---至今     四川大学化学学院从事教学和科研

主要研究方向

1. 具有重要生物活性的复杂天然产物全合成

2. 天然产物分子探针的生物学功能开发

3. 合成导向的反应方法学研究

4. 药物合成 科研项目

 

1. 天然产物全合成,国家杰出青年科学基金,2020-2024

2. 具微管稳定活性的taccalonolides天然产物的合成研究,国家自然科学基金面上项目(2019-2022)

3.基于去芳香化/[5+2]环加成策略的二萜及其类天然产物合成研究,国家自然科学基金面上项目(2017-2020

4.具有重要药用价值的多环天然产物的高效合成,国家自然科学基金重大项目(2013-2017)。

5.瑞香烷型二萜Trigoxyphin A的全合成研究,国家自然科学基金面上项目(2012-2015),项目负责人。

6.具有重要生物活性的天然产物的化学合成,国家重点基础研究计划(科技部973计划, 2010-2014)。

7.四川大学优秀青年学者科研基金(B类),2011-2014

8.天然产物Chlorahololide A(钾离子通道抑制剂)的全合成研究,国家自然科学基金面上项目(2009-2011),项目负责人。

9.教育部新世纪优秀人才支持计划(2009-2011, 项目负责人。

10.抗真菌天然产物金粟兰内酯 A 的全合成研究,教育部留学回国人员基金(2009-2011),项目负责人。

11.抗结核天然产物Hirsutellones A-F 的全合成研究,国家自然科学基金青年基金项目(2008-2010),项目负责人。

主要工作业绩

刘波教授以萜类复杂天然产物为目标,借助仿生合成策略,结合串联反应和一锅多组分反应,开展目标分子的高效全合成和相关合成方法学研究;从全合成中获得的反应活性和选择性等信息的基础上,提出和完善天然产物的生源假说,具体包括:

1. 乌药烷天然产物的全合成及其生源假说的完善

从我国中药金粟兰科植物分离出的乌药烷倍半萜化合物,结构独特且具有多种生物活性,是金粟兰科植物的标志性化合物。该类天然产物近年来引起了合成化学家们的关注。

刘波教授通过阶梯式方式实现了乌药烷系列天然产物的合成(图一)2011年,刘波教授实现了乌药烷倍半萜单体Chloranthalactone A的全合成,这是该类天然产物的首次全合成;在此基础上,刘波教授完成了其他乌药烷倍半萜和[2+2]型二聚体的发散式合成。之后,刘波教授修改文献中的生源假说,采用仿生策略仅用14步,首次实现乌药烷二倍半萜 bolivianine isobilivinine 的全合成,之后进一步将合成短至12步。Chemistry World 专栏作家 Phillip Broadwith高度评价该工作 (Chemistry World, June 272013)通过传统合成方法完成 bolivianine 这样复杂的分子已具有足够的挑战,而通过仿生合成途径不仅挑战大而且是有益的,刘小组不仅完成了这样一个复杂分子的合成,而且使提出的生源合成路线更加可信。”2017年,刘波教授以仿生酸催化[4+2]环加成为关键策略,实现了乌药烷倍半萜二聚体 Shizukaol D Sarcandrolide J的全合成,这是自1990年被分离以来,[4+2]型乌药烷倍半萜二聚体的首次全合成,在该合成中,刘波教授提出并验证了新的生源合成假说。2019年,针对第一代酸催化下仅能实现一种类型二聚体合成的局限,刘波教授发展了碱性条件下的第二代合成策略,新策略实现了三种类型乌药烷倍半萜二聚体的发散式全合成。

在乌药烷合成研究中,刘波教授还发展了多个方法学工作,包括钯催化分子内环丙烷化,缩酮脱保护以及羟胺氧化断裂构建羧酸()。基于上述工作,刘波教授应邀撰写乌药烷天然产物合成进展的综述论文 (Chin. J. Org. Chem., 2013, 33, 90.)

 

 

图一 乌药烷倍半萜单体及其二聚体的合成

二.多环二萜及二倍半萜天然产物的全合成

自然界广泛存在的二萜及二倍半萜具有复杂的化学结构和多样的生物活性,研究合成这些天然产物对于认识和开发利用这类化合物具有重要意义。刘波教授完成了阿替烷、松香烷、罗汉松烷、桃柁烷和半日花烷型等一系列二萜及二倍半萜天然产物的全合成。刘波教授还从环己烯内酯出发,以Michael/aldol加成和氧杂Michael加成/消除为关键策略,完成了二倍半萜leucosceptroid B的首次全合成 (图二, a),并进一步完成了对这类天然产物家族中leucosceptroid FG的合成。刘波教授还从香叶基溴出发,以未保护邻苯二醌的分子间Diels-Alder反应和酸促进仿生串联重排反应为关键策略(图二, b),完成了多个阿替烷二萜天然产物的全合成,

 

 

图 二  二萜及二倍半萜类天然产物的全合成

 

 

图三 二萜类天然产物的全合成

 

建立了经典阿替烷与重排阿替烷化合物之间的生源关系;同时,刘波教授还发展了Diels-Alder/光照脱羰基构建罗汉松烷二萜衍生物的方法。在实现二萜天然产物半日花烷二烯半合成的基础上,刘波教授利用HAT多烯环化的策略完成了该片段的全合成,并以此为基础与亲双烯体在室温下发生仿生Diels-Alder反应,实现了hispidanin A的并列首次全合成(图三),提出并验证了与文献不同的非酶催化的[4+2]环加成生源途径。Maimone教授对该工作评价道 (Nat. Prod. Rep., 2018, 35, 174.)Liu等合成hispidanin A的工作中,氢原子转移诱导自由基多烯环化反应毫无疑问地显示出了这个化学合成策略在立体选择性的合成多环化合物的潜力。

刘波教授独立工作以来完成近50个分子的合成工作(图四和图五),以通讯作者发表50多篇SCI论文(包括2JACS, 3ACIE1Nature. Commun.);在国内外学术会议作邀请报告37次,口头报告4次;在Elsevier出版的Strategies and Tactics in Organic Synthesis一书中撰写第7章;2009年获教育部新世纪优秀人才支持计划;2013年获国家优秀青年科学基金资助;2014年获Thieme Chemistry Journal Award2015年获中国化学会维善合成化学奖;201520162018年获 ACP Lectureship Awards; 2019年获国家杰出青年科学基金资助。

 

 

 

图四 刘波教授完成的天然产物分子(2010-2017)

 

 

图五 刘波教授完成的天然产物分子(2017-2019)

获得奖励

教育部新世纪优秀人才支持计划(2009

国家自然科学基金委优秀青年科学基金(2013

Thieme Chemistry Journal Award 2014

ACP Lectureship Awards to Japan & Malaysia (2014)

ACP Lectureship Awards to Taiwan (2015)

中国化学会维善天然产物合成奖(2015

ACP Lectureship Awards to Singapore (2016)

国家自然科学基金委杰出青年科学基金(2019

代表性成果

(获奖成果、专著、论文、专利)

1. Biao Du, Zhengsong Huang,Xiao Wang,   Ting Chen, Ying Sun, ShaominFu and Bo Liu.* Nature. Commun. 2019, 10, 1892.

     ·Highlighted by CBG News.

 

2. Heping Deng, Wei Cao, Rong Liu, Yanhui Zhang, and Bo Liu*, Asymmetric Total Synthesis of Hispidanin A, Angew. Chem. Int. Ed., 2017, 56, 5849-5852.   

·Selected as Hot paper    

·Highlighted by Advanced Science News  

 

3. Changchun Yuan, Biao Du, Heping Deng, Yi Man, Bo Liu*, Total Synthesis of Sarcandrolide J and Shizukaol D: Lindenane Sesquiterpenoid [4+2] Dimers, Angew. Chem. Int. Ed., 2017, 56, 637-640.   

·Highlighted by Synfacts (2017, 227)

·Selected as Synfact of the month ·Highlighted by X-MOL

·Highlighted by Chin. J. Org. Chem.(有机化学,2017, 37, 774

 

4. Liqiang Song, Guili Zhu, Yongjiang Liu, Bo Liu*, Song Qin, Total Synthesis of Atisane-type Diterpenoids: Application of Diels-Alder Cycloadditions of Podocarpane-type Unmaskedortho-Benzoquinones, J. Am. Chem. Soc. 2015, 137, 13706-13714.    

·Highlighted by Synfacts (2016, 6)    

·Highlighted by X-MOL

 

5. Changchun Yuan, Biao Du, Li Yang, Bo Liu* Bioinspired Total Synthesis of Bolivianine: A Diels-Alder/ Intramolecular Hetero-Diels-Alder Cascade Approach, J. Am. Chem. Soc.2013, 135, 9291-9294.    

·One of Most Read Articles inJ. Am. Chem. Soc.

·Highlighted by Synfacts (2013, 915)

·Selected as Synfact of the month

·Highlighted by Chin. J. Org. Chem.(有机化学,2013, 33, 2028

·Highlighted by RSC/Chemistry World (2013-06-27)  

 

6. Xuan Huang, Liqiang Song, Jiao Xu, Guili Zhu, Bo Liu* Asymmetric Total Synthesis of Leucosceptroid B, Angew. Chem. Int. Ed.2013, 52, 952-955.  

·Highlighted by Synfacts (2013, 246)

·Highlighted by Chin. J. Org. Chem.(有机化学,2013,33, 654

 

7. Guili Zhu, Chengying Zhou, Song Chen, Shaomin Fu*, Bo Liu*. Org. Lett., 2019, 19, 7809.

8. Song Chen, Ting Chen, Guanggen Liu, Xiao Wang, Guili Zhu, Yongjiang Liu, Shaomin Fu* and Bo Liu*.Org. Biomol. Chem., 2019, 17,4711.

 

9. Ting Chen, Song Chen, Shaomin Fu *, Song Qin, Bo Liu*. Carbon-oxygen homo-coupling of 2-naphthols through electrochemical oxidative dearomatization. Synlett., 2019, 30, 903.

 

10. Rong Liu, Mengwei Xia, Yanhui Zhang, Shaomin Fu*, Bo Liu*. The Journey of Total Synthesis Toward Nannocystin Ax. Tetrahedron, 2019, 75, 1781-1794. Zhou Weishan Issue.

 

11.Yongjiang Liu, Yanhui Zhang, Xiao Wang, Shaomin Fu*, Bo Liu*. Synthesis of polycyclic frameworks through Iron-catalyzed intramolecular [5+2] cycloaddition. Synlett, 2018, 29(15): 1978. 

 

12.Yi Man, Shaomin Fu*, Juan Chen, and Bo Liu*. Total synthesis and structural revision of an isopanepoxydone analog isolated from Lentinus strigellus. Org. Biomol. Chem., 2018, 16, 5043-5049.

 

13.Jing Feng, Tianzi Yu, Zhijiang Zhang, Jinpeng Li, Shaomin Fu, Juan Chen, and Bo Liu *.Asymmetric synthesis of the fully functionalized six-membered ring of trigoxyphin A. Chem. Comm., 2018, 54, 7665-7668.

● Highlighted by X-MOL

 

14.Jing Feng, Hongli Yin, Yi Man, Shaomin Fu* and Bo Liu*. Asymmetric Synthesis of the Ring A Substructure of Genkwadane A. Chin. J. Chem. 2018, 36, 831-836.

● Selected as back cover paper.

 

15.Man Yi, Bo Liu. Progress in Total Syntheses of Anti‐malignant Pleural Mesothelioma Compounds. J. Chin. Chem. Soc., 2018, 65(3), 301-311.

16.Yongjiang Liu, Xiao Wang, Song Chen, Shaomin Fu and Bo Liu*. Iron-Catalyzed Intramolecular Perezone-Type [5+2] Cyclo- addition: An Access to Tricyclo[6.3.1.01,6]dodecane. Org.Lett., 2018, 20(10), 2934-2938.  

 

17. Asymmetric Synthesis of Hispidanin A and the Related Diterpenoids.Wei Cao, Heping Deng, Ying Sun, Bo Liu, Song Qin.;Chem. Eur. J., 2018, 24, 9120-9129.

 

18. Chen, Juan; Liu, Bo:Total Synthesis of Natural Terpenoids: Inspired but Not Limited by Biohypothesis Synlett, 2018, 29(7), 863.

 

19. Ze Meng, Bo Liu*, Total synthesis of five natural eremophilane-type sesquiterpenoids, Org. Biomol. Chem., 2018, 16, 957-962.

 

20. Changchun Yuan*, Bo Liu*, Total Synthesis of Natural Products via Iridium Catalysis, Org. Chem. Front., 2018, 5, 106-131.

 

21.Yan-Hui Zhang, Rong Liu, Bo Liu*Total Synthesis of Nannocystin Ax, Chem. Commun., 2017, 53, 5549-5552.

 

22. Changchun Yuan, Biao Du, Miao-Miao Xun, Bo Liu*, Oxidative Cleavage of Hydroxamic Acid Promoted by Sodium Periodate, Tetrahedron, 2017, 73, 3622-3628.

 

23. Guili Zhu, Bo Liu*, Synthesis of derivatives of podocarpane-type diterpenoids through Diels-Alder cycloaddition and photo-decarbonylation from unmasked ortho-benzoquinone, Tetrahedron, 2017, 73, 4070-4075.

 

 

24. Guili Zhu, Sachin B. Wadavrao, Bo Liu*, Divergent total synthesis of atisane-type diterpenoids, Chem. Rec., 2017, 17, 584-596.

 

25.  Zhijiang Zhang, Bo Liu*, Total synthesis and confirmation of the revised structures of jiangrines A, C and D, Org. Biomol. Chem., 2017, 15, 207-212.

 

26. Jinpeng Li, Changchun Yuan, Biao Du, Bo Liu*, an Alternative Total Synthesis of Bolivianine, Chin. Chem. Lett. 2017, 28, 113-116.

 

27. Zhijiang Zhang, Bo Liu*, Total Synthesis of Proposed Structures of Jiangrines C and D, Sci. Chin. Chem. 2016, 59, 1205-1210.

 

28. Hongli Yin, Zhe Meng, Bo Liu*, Construction of the Core Structure of Trichotomone, Synthesis, 2016, 48, 3951-3956.

 

29. Heping Deng, Wei Cao, Zhijiang Zhang, Bo Liu*, Asymmetric Synthesis and Absolute Stereochemistry of A Labdane-type Diterpenoid Isolated from the Rhizomes of Isodan yuennanensis, Org. Biomol. Chem. 2016, 14, 6225-6230.

 

30. Li Yang, Liqiang Song, Chong Huang, Mingzheng Huang, Bo Liu*, Exploiting Ortho- Substitution Effect on Formation of Oxygen-containing [10]Paracyclophane through Ring-Closing Metathesis, Org. Chem. Front. 2016, 3, 319-323.

 

31. Rong Liu, Jing Feng, Bo Liu*, Synthetic Progress of Daphnane-type Diterpenoids, Acta Chim. Sin 2016, 74, 24-43.

 

32. Tianzi Yu, Bo Liu*, Asymmetric Total Synthesis of 3-Furanoeudesmene, A Metabolite from Antarctic Gorgonian and Determination of Its Absolute Configuration, Chin. J. Org. Chem. 2015, 35, 2157-2161

 

33. Jiao Xu, Bo Liu* Total synthesis of norleucosceptroids F and G, Chin. Chem. Lett. 2015, 26, 1341–1344.

 

34. Guili Zhu, Rong Liu, Bo Liu*, Total Synthesis of Atisane-type Diterpenoids and Related Diterpenoid Alkaloids, Synthesis 2015, 47, 2691-2708. (Invited review) 

 

35. Li Yang, Jing Feng, Jinpeng Li, Bo Liu*, Total synthesis of heliespirone B, Tetrahedron Lett. 2015, 56, 4931-4933.

 

36. Liqiang Song, Chong Huang, Mingzheng Huang, Bo Liu*, Toward the synthesis of hirsutellone B via an intramolecular Diels-Alder /ketene-trapping strategy, Tetrahedron 2015, 71, 3603-3608.

 

37. Yang Yang, Jinpeng Li, Biao Du, Changchun Yuan, Bo Liu*, Song Qin*, An Entry to Vinylcyclopropane through Palladium-catalyzed Intramolecular Cyclopropanation of Alkenes with Unstabilized Allylic tosylhydrazones, Chem. Commun. 2015, 51, 6179-6182. 

 

38. Jing Feng, Bo Liu*, Formal Carbo [3+3] Annulation and Its Application in Organic Synthesis, Tetrahedron Lett. 2015, 56, 1474-1485.

 

39. Li Yang, Guizhou Yue, Changchun Yuan, Biao Du, Heping Deng, Bo Liu*, Synthetic Studies toward Lindenane-Type Sesquiterpenoid Dimers, Synlett 2014, 25, 2471-2474.

 

40. Hai Tong, Bo Liu*, A Diels-Alder Approach toward the scaffolds of Polycyclic sesquiterpenoids with 2-Pyrone, Synlett 2014, 25, 681-686.

 

41. Biao Du, Changchun Yuan, Tianzi Yu, Li Yang, Yang Yang, Bo Liu*, Song Qin* Asymmetric Total Synthesis of Onoseriolide, Bolivianine and Isobolivianine, Chem. Eur. J. 2014, 20, 2613-2622.

 

42. Biao Du, Changchun Yuan, Langzhong Zhang, Li Yang, Bo Liu* Deprotection of 1,3-Oxathiolanes to Ketones Promoted by Base, Tetrahedron Lett. 2013, 54, 2217-2220.

 

43. Guizhou Yue, Xuan Huang, Bo Liu* Progress in the Total Synthesis of trans-Hydrindane- Containing Terpenoids, Chin. J. Org. Chem. 2013, 33, 1167-1185.

 

44. Jing Feng, Guili Zhu, Bo Liu*, Xiangdong Zhou* Expedient Synthesis of (R)-Curcuphenol: A Chiral Pool Strategy, Chin. J. Chem. 2013, 31, 23-26.

 

45. Guizhou Yue, Li Yang, Changchun Yuan, Biao Du, Bo Liu* Progress in Total Syntheses of Lindenane-type Sesquiterpenoids and Their Dimers, Chin. J. Org. Chem. 2013, 33, 90-100.

 

46. Hang Su, Ting Zhou, Bo Liu* Total Synthesis of (±)-Spirobenzofuran, Synlett 2013, 615-618.

 

47. Changchun Yuan, Li Yang, Biao Du, Bo Liu* A Base-promoted deprotection of 1, 3-dioxolanes to ketones, Tetrahedron Lett. 2012, 53, 6972-6976.

 

48. Guizhou Yue, Li Yang, Changchun Yuan, Biao Du, Bo Liu* Total Syntheses of Lindenane- type Sesquiterpenoids: (±)-Chloranthalactones A, B, F, (±)-9-Hydroxy Heterogorgiolide and (±)-Shizukanolide E, Tetrahedron, 2012, 68, 9624-9637.

 

49. Ting Zhou, Guili Zhu, Xuan Huang, Bo Liu* Zeise’s dimmer-catalyzed regioselective hydration of homopropargyl tertiary ether, Tetrahedron Lett. 2012, 53, 4955-4958

 

50. Guizhou Yue, Li Yang, Changchun Yuan, Xiaoling Jiang, Bo Liu* Total synthesis of chloranthalactone A, Org. Lett. 2011, 13, 5406-5408. (one of Most Read Articles of OL in September, 2011)

 

51. Yongjiang Liu, Chong Huang, Bo Liu* Asymmetric total syntheses of heliannuol E and epi-heliannuol E, Tetrahedron Lett. 2011, 52, 5802-5804.

 

52. Chong Huang, Wenhan Zhang, Bo Liu* Racemic and enantioselective total synthesis of heliespirones A & C, Sci. China. Chem. 2011, 54, 43-55.

 

53. Mingzheng Huang, Liqiang Song, Bo Liu* Construction of the Cyclophane Core of the Hirsutellones via a RCM Strategy, Org. Lett. 2010, 12, 2504-2507.

 

54. Chong Huang, Bo Liu* Asymmetric total synthesis ent-heliespirones A & C, Chem. Commun. 2010, 46, 5280-5282.

 

55. Daxing Yang, Jianfeng Huang, Bo Liu* Platinum-Catalyzed Regioselective Formation of β-Alkoxy Ketones from Internal Alkynes, Eur. J. Org. Chem. 2010, 4185-4188.

 

 

56. Jianfeng Huang, Xuan Huang, Bo Liu* Gold-catalyzed synthesis of nitrogen-containing heterocycles from ε-N-protected propargylic esters, Org. Biomol. Chem. 2010, 8, 2697-2699.

 

57. Yunxiu Chen, Jianfeng Huang, Bo Liu* Total syntheses of the proposed structures of cuevaene A, Tetrahedron Lett. 2010, 51, 4655-4657.

 

58. Mingzheng Huang, Chong Huang, Bo Liu* Studies toward the total synthesis of the hirsutellones, Tetrahedron Lett. 2009, 50, 2797-2800.

 

Postdoctoral, Graduate and Undergraduate

 

59. Jef K. De Brabander*, Bo Liu, Mingxing Qian Au(I)- and Pt(II)-Catalyzed Cyclo- etherification of ω-Hydroxy Propargylic Esters, Org. Lett. 2008, 10, 2533.

60. Xin Jiang, Bo Liu, Sylvain Lebreton, Jef K. De Brabander* Total Synthesis and Structure Revision of the Marine Metabolite Palmerolide A, J. Am. Chem. Soc. 2007, 129, 6386. (One of the Most-Accessed Articles in 2007

61. Bo Liu, Jef K. De Brabander* Metal-Catalyzed Regioselective Oxy-Functionalization of Internal Alkynes: An Entry into Ketones, Acetals, and Spiroketals, Org. Lett. 2006, 8, 4907.

62. De-Run Li, Dong-Hui Zhang, Cai-Yun Sun, Ji-Wen Zhang, Li Yang, Jian Chen, Bo Liu, Ce Su, Wei-Shan Zhou*, Guo-Qiang Lin* Total Synthesis of Phorboxazole B, Chem. Eur. J. 2006, 12, 1185.

63. Bo Liu, Wei-Shan Zhou* Towards the total synthesis of natural peloruside A: stereoselective synthesis of the backbone of the core, Org. Lett. 2004, 6, 71.

 

64. Bo Liu, Wei-Shan Zhou*, Stereoselective synthesis of the C21-C27 fragment of the phorboxazoles, Tetrahedron Lett. 2003, 44, 4933.

 

65. Bo Liu, Wei-Shan Zhou* The first stereoselective synthesis of orostanal, a novel abeo-sterol inducing apoptosis in leukemia cells, Tetrahedron 2003, 59, 3379.

 

66.Zhigang Jiao, Xiaoming Feng * , Bo Liu , Fuxue Chen, Guolin Zhang, Yaozhong Jiang, Enantioselective Strecker reactions between aldimines and trimethylsilyl cyanide promoted by chiral N,N’-dioxides, Eur. J. Org. Chem. 2003 , 3818.

 

67. Bo Liu, Wei-Shan Zhou* The first stereoselective synthesis of orostanal, a novel abeo-sterol inducing apoptosis in leukemia cells, Tetrahedron Lett. 2002, 43, 4187.

 

68. Bo Liu, Xiaoming Feng*, Fuxue Chen, Guolin Zhang, Xin Cui, Yaozhong Jiang, Enantio- selective Strecker reaction promoted by chiral N –oxides, Synlett 2001, 1551.

 

Book Chapter

Bo Liu, Changchun Yuan, Biao Du in Strategies and Tactics in Organic Synthesis, Vol. 13 (Eds.: Michael Harmata), Elsevier, 2017, p. 161-216 Chapter 7

 

 

Patent

Jef K. De Brabander, Xin Jiang, Bo LiuPalmerolides: Methods of preparation and derivatives thereof, US patent, US2008249162-A1; WO2008124072-A1; TW200906387-A; US7838691-B2.

 

关闭