今天是:2017年9月24日 星期日 农历八月初五
宋振雷 教授 (博士生导师)
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宋振雷   教授 博士生导师                         

 

联系方式

通讯地址:成都市人民南路三段17# 四川大学华西药学院,610041

联系电话:028-85501876

电子邮箱E-mail: zhenleisong@scu.edu.cnzhenleisong@hotmail.com

课题组网站:www.zhenleisonggroup.com

 

教育背景

1996-2000 兰州大学化学系基地班,本科。

2000-2005 兰州大学化学系有机化学专业硕博连读,师从中国科学院院士涂永强教授。

2005-2008 美国明尼苏达大学化学系,后转至威斯康星大学麦迪逊分校药学院博士后,师从Richard. P Hsung 教授。

2008-2012 四川大学华西药学院, 副教授。

2012-至今 四川大学华西药学院,教授。

 

任职

2012-2013四川大学华西药学院,科研秘书。

2013-2014四川大学华西药学院,院长助理。

2014-至今 四川大学华西药学院,科研副院长。

 

曾获奖项

12008年四川省卫生厅第八批学术技术带头人后备人选

220092011年度四川大学优秀青年骨干教师奖励

32012年四川大学引进人才(2008年进校)优秀

42012教育部新世纪优秀人才支持计划

52013中国化学会青年化学奖

62014 Asian Core Program Lectureship Award

72017年国家自然科学基金优青项目获得者

 

科研项目

1国家自然科学基金青年基金Silicon-Tethered分子内Corey-ChaykovskyTandem Heterocyclopropylolefin环化反应研究2009-2011,主持

2、国家自然科学基金面上项目:双硅化合物反应及天然产物合成应用研究 2012-2015,主持

3教育部新世纪优秀人才支持计划:天然产物及药物合成2013-2015主持

4国家自然科学基金优青项目:有机硅化学2017-2019主持

5、教育部高校博士点新教师基金:“Silicon-Tethered的分子内Corey-Chaykovsky反应研究” 2009-2011,主持

6四川大学优秀青年学者科研基金双硅化合物反应及天然产物合成应用研究 2011-2014,主持

7科技部973课题:重要天然产物的仿生和生物合成 2010-2014,学术骨干

8、国家自然科学基金创新群体科学基金项目:高选择性的有机合成新反应与新策略” 2011-2016,学术骨干

9、国家自然科学基金委重大项目:具有重要药用价值的多环天然产物高效合成” 2013-2017,学术骨干

 

研究课题

课题组专注于新型功能性有机硅分子的开发、反应及应用研究。近年来围绕结构新颖的功能性有机硅合成子??偕双硅[Geminal Bis(silane)]开展了系统的研究,并取得了以下三个方面的进展:(1)解决了构建偕双硅这一空间极度拥挤结构的挑战性难题,开发了偕双硅烯醇衍生物、烯醛、二烯、高烯丙醇等结构多样的偕双硅合成子,实现了功能性偕双硅多样、实用的高效合成。(2)系统地探明了偕双硅所蕴含的立体效应、电子效应、硅迁移、双官能团性等特殊性质和功能,发展了十多类新颖的偕双硅反应方法学,实现了几类常规化学、区域和立体选择性的有效反转,解决了分子间Diels-Alder反应exo-选择性控制、大位阻结构去质子化、远距离[1,5]-硅迁移、以及cis-Z四氢吡喃环构建等若干合成难题。(3)以偕双硅反应方法学为关键策略,实现了(-)-ExiguolideNematocidal Oxylid的全合成,以及明星天然产物Bryostatins BC环的高效构建,凸显了偕双硅合成子及化学的重要应用价值。

             

发表论文

2008-至今

55. Chu, Y.; Pu, Q.; Tang, Z. X.; Gao, L.; Song, Z. L.* Enantioselective Synthesis of Crotyl Geminal Bis(silane) and Its Usage for Asymmetric Sakurai Allylation of Acetals Tetrahedron Lett. 2017, ASAP.

 

54. Chu, Z. W.; Wang, K.; Gao, L.; Song, Z. L.* Chiral Crotyl Geminal Bis(silane): A Useful Reagent for Asymmetric Sakurai Allylation by Selective Desilylation-enabled Chirality Transfer Chem. Commun. 2017, 53(21), 3078-3081.

 

53. Hu, J.; Gao, L.*; Song, Z. L.* Study on Regio- and Diastereoselective Epoxide Opening/Halogenation of Geminal Bis(silyl) 2,3-Epoxy Alcohols Chinese Journal of Synthetic Chemistry, 2017, 25(4), 277-281.

 

52. Liu, Z. J.; Lin, X. L.; Yang, N.; Su, Z. S.*; Hu, C. W.; Xiao, P. H.; He, Y. Y.; Song, Z. L.* Unique Steric Effect of Geminal Bis(silane) to Control the High Exo-selectivity in Intermolecular Diels-Alder Reaction J. Am. Soc. Chem. 2016, 138(6), 1877-1883.

 

51. Lin, X. L.; Gan, Z. B.; Lu, J.; Su, Z. S.; Hu, C. W.; Zhang, Y. B.; Wu, Y.; Gao, L.*; Song, Z. L.* Visible Light-promoted Radical Cyclization of Silicon-tethered Alkyl Iodide and Phenyl Alkyne. An Efficient Approach to Synthesize Benzosilolines Chem. Commun. 2016, 52(36), 6189-6192.

 

50. Gan, Z. B.; Chu, Z. W.; Hu, J.; Su, Z. S.; Hu, C. W.; Gao, L.; Song, Z. L.* Tunable Reactivity of Geminal Bis(silyl) Enol Derivatives Leading to Selective exo-IEDDA or Sakurai Allylation with a β,γ-Unsaturated Ketoester Chem. Commun. 2016, 52(66), 10137-10140.

 

49. Huang, Z. G.; Gao, L.*; Song, Z. L.* Asymmetric Alkylation or Silylation of (S)-(–)-Diphenylprolinol-derived α-Silyl Amide to Synthesize Optically Pure α-Monosilyl or Bis(silyl) Amides Tetrahedron Lett. 2016, 57(26), 2861-2864.

 

48. Li, H. Z.; Xie, H. M.; Zhang, Z. G.; Xu, Y. J.; Lu, J.; Gao, L.; Song, Z. L.* Total Synthesis of ()-Exiguolide via an Organosilane-based Strategy Chem. Commun 2015, 51(40), 8484-8487.

 

47. Li, L. J.?; Sun, X. W.?; He, Y. Y.; Gao, L.; Song, Z. L.* TMSBr/InBr3-promoted Prins Cyclization/Homobromination of Dienyl Alcohol with Aldehyde to Construct cis-THP Containing an Exocyclic E-Alkene Chem. Commun 2015, 51(80), 14925-14928. (The 3rd most downloaded article between July-Sept. 2015)

 

46 Li, L. J.; Chu, Y.; Gao, L.; Song, Z. L.* Geminal Bis(silane)-controlled Regio- and Stereoselective Oxidative Heck Reaction of Enolethers with Terminal Alkenes to Give Push-pull 1,3-Dienes Chem. Commun 2015, 51(85), 15546-15549.

 

45. Xu, Y. J.?; Yin, Z. P.?; Lin, X. L.; Gan, Z. B.; He, Y. Y.; Gao, L.; Song, Z. L.* 1,4-Hydroiodination of Dienyl Alcohols with TMSI to Form Homoallylic Alcohols Containing a Multisubstituted Z-Alkene and Application to Prins Cyclization. Org. Lett. 2015, 17(8), 1846-1849.

 

44. Yin, Z. P.; Liu, Z. J.; Huang, Z. G.; Chu, Y.; Chu, Z. W.; Hu, J.; Gao, L.*; Song, Z. L.* Synthesis of Functionalized γ-Lactone via Sakurai exo-Cyclization/Rearrangement of 3,3-Bis(silyl) Enol Ester with a Tethered Acetal. Org. Lett. 2015, 17(6), 1553-1556.

 

43. Zhang, Z. G.?; Xie, H. M.?; Li, H. Z.; Gao, L.; Song, Z. L.* Total Synthesis of (–)-Exiguolide. Org. Lett. 2015, 17(19), 4706-4709.

 

42. Li, L. J.; Zhang, Y. B.; Gao, L.*; Song, Z. L.* Recent Advances in C-Si Bond Activation via a Direct Transition Metal Insertion. Tetrahedron Lett. 2015, 56(12), 1466-1473.

 

41. Wu, Y.; Gao, L.*; Song, Z. L.* Recent Advances in Silicon-stereogenic Chiral Organosilanes. Chemistry, 2015, 78, 676-680.

 

40. Wu, Y.; Li, L. J.; Li, H. Z.; Gao, L.; Xie, H. M.; Zhang, Z. G.; Su, Z. S.; Hu, C. W.*; Song, Z. L.* Regioselective Nucleophilic Addition of Organometallic Reagents to 3?Geminal Bis(silyl) N?Acyl Pyridinium Org. Lett. 2014, 16(7), 1880-1883. [Highlight in SYNFACTS, 2014, 10, 0743].

 

39. Lin, X. L.; Ye, X. C.; Sun, X. W.; Zhang, Y. B. Gao, L.; Song, Z. L.* [1,5]-Anion Relay via Intramolecular Proton Transfer To Generate 3,3-Bis(silyl) Allyloxy Lithium: A Useful Scaffold for Syn-Addition to Aldehydes and Ketones Org. Lett. 2014, 16(4), 1084-1087 [Highlight in SYNFACTS, 2014, 10, 0522.].

 

38. Sun, C. Z.?; Zhang, Y. B.?; Xiao, P. H.; Li, H. Z.; Sun, X. W.; Song, Z. L.* Intramolecular [1,4]-S- to O?Silyl Migration: A Useful Strategy for Synthesizing Z?Silyl Enol Ethers with Diverse Thioether Linkages. Org. Lett. 2014, 16(3), 984-987.

 

37. Ye, X. C.; Sun, X. W.; Huang, Z. G.; Yang, N.; Su, Z. S.; Hu, C. W.; Song, Z. L.* Regioselective 1,4- Over 1,2-Addition of 3,3-Bis(silyl) Allyloxy Lithium to Enals, Enones and Enoates. The Remarkable α-Effect of Silicon. Org. Biomol. Chem. 2014, 12(19), 3021-3025.

 

36. Gao, L.; Lu, J.; Song, Z. L.*; Lin, X. L.: Xu, Y. J.; Yin, Z. P. [1,5]-Brook Rearrangement: An Overlooked but Valuable Silyl Migration to Synthesize Configurationally Defined Vinylsilane. The Unique Steric and Electronic Effects of Geminal Bis(silane) Chem. Commun. 2013, 49(79), 8961-8963.

 

35. Gao, L.; Lu, J.; Song, Z. L.* Recent Efforts to Construct The B-Ring of Bryostatins Chem. Commun. 2013, 49(87), 10211-10220. (Invited Feature Article)

 

34. Li, L. J.; Ye, X. C,; Wu, Y.; Gao, L.; Song, Z. L.*; Yin, Z. P.; Xu, Y. J. Sakurai Reaction of 3,3-Bis(silyl) Silyl Enol Ethers with Acetals Involving Selective Desilylation of the Geminal Bis(silane). Concise Synthesis of Nematocidal Oxylipid Org. Lett. 2013, 15(5), 1068-1071.

 

33. Yan, L. J.; Sun, X. W.; Li, H. Z.; Song, Z. L.*; Liu, Z. J. Geminal Bis(silyl) Enal: A Versatile Scaffold for Stereoselective Synthesizing C3,O1-Disilylated Allylic Alcohols Based upon Anion Relay Chemistry Org. Lett. 2013, 15(5), 1104-1107.

 

32. Sun, X. W.; Song, Z. L.*; Li, H. Z.; Sun, C. Z. [1,4]-S- to O-Silyl Migration: Multicomponent Synthesis of α-Thioketones through Chemoselective Transformation of Esters to Ketones with Organolithium Reagents. Chem. Eur. J. 2013, 19(51), 17589-17594.

 

31. Gao, L.; Zhang, Y. B.; Song, Z. L.* Exploration of Versatile Geminal Bis(silane) Chemistry Synlett 2013, 24(2), 139-144. (Invited SYNPACT Article)

 

30. Lu, J.; Song, Z. L.*; Zhang, Y. B.; Gan, Z. B.; Li, H. Z. Prins Cyclization of Bis(silyl) Homoallylic Alcohols to Form 2,6-cis-Tetrahydropyrans Containing a Geometrically Defined Exocyclic Vinylsilane: Efficient Synthesis of Ring B of the Bryostatins Angew. Chem. Int. Ed. 2012, 51(22), 5367-5370. [Highlight in Org. Chem. Highlights 2013, January 14; Chin. J. Org. Chem. 2012, 32, 1553.]

 

29. Sun, X. W.?; Lei, J.?; Sun, C. Z.; Song, Z. L.*; Yan. L. J. [1,5]-Anion Relay/[2,3]- Wittig Rearrangement of 3,3-Bis(silyl) Allyl Enol Ethers: Synthesis of Useful Vinyl Bis(silane) Species Org. Lett. 2012, 14(4), 1094-1097. [Highlight in SYNFACTS, 2012, 8, 0544.]

 

28. Gao, L.; Lin, X. L.; Lei, J.; Song, Z. L.*; Lin, Z. Bissilyl Enal: A Useful Linchpin for Synthesis of Functionalized Vinylsilane Species by Anion Relay Chemistry

Org. Lett. 2012, 14(1), 158-161.

 

27. Gan, Z. B.; Wu, Y.; Gao, L.; Sun, X. W.; Lei, J.; Song, Z. L.*; Li, L. J.. Studies on retro-[1,4] Brook Rearrangement of 3-Silyl Allyloxysilanes. Observation of the Formation of Unusual 3,3-Bissilyl Enols Tetrahedron 2012, 68(34), 6928-6934.

 

26. Song, Z. L.; Fan, C. A.; Tu, Y. Q.* Semipinacol Rearrangement in Natural Product Synthesis Chem. Rev. 2011, 111(11), 7523-7556.

 

25. Song, Z. L.*; Kui, L. Z.; Sun, X. W.; Li, L. J. Addition of TMS-Substituted Oxiranyl Anions to Acylsilanes. A Highly Stereoselective Approach to Tetrasubstituted (Z)-β- Hydroxy-α-TMS Silyl Enol Ethers Org. Lett. 2011, 13(6), 1440-1443.

 

24. Wang, C.; Gan, Z. B.; Lu, J.; Wu, X.; Song, Z. L.* A Highly Stereoselective Approach to Tetrasubstituted (E)-β-Hydroxy Silyl Enol Ethers by Addition of Aryl-Substituted Oxiranyl Anions to Acylsilanes Tetrahedron Lett. 2011, 52(19), 2462-2464.

 

23. Wu, X.; Lei, J.; Song, Z. L.* Synthesis of Cyclic β-Silylenones via Oxidative Rearrangement of Tertiary α-Hydroxy Allylsilanes with PCC Chinese. Chem. Lett. 2011, 22(3), 306-309.

 

22. Song, Z. L.*; Lei, Z; Gao, L.; Wu, X.; Li, L. J. Efficient Approach to 3,3-Bissilyl Carbonyl and Enol Derivatives via Retro-[1,4] Brook Rearrangement of 3-Silyl Allyloxysilanes Org. Lett. 2010, 12(22), 5298-5301. [Highlight in SYNFACTS, 2011 (2), 0194.]

 

21. Song, Z. L.*; Lohseb, A. G.; Hsung, R. P.* Challenges in the synthesis of a unique mono-carboxylic acid antibiotic, (+)-zincophorin. Nat. Prod. Rep. 2009, 26, 560-571.

 

博士及博士后

20. Kenealey, J. D.; Subramanian, L.; Van Ginkel, P. R.; Darjatmoko, S.; Lindstrom, M. J.; Somoza,V.; Ghosh, S. K.; Song, Z. L.; Hsung, R. P.; Kwon, G. S.; Eliceiri, K.; Albert, D. M.; Polans, A. S. Resveratrol Metabolites Do Nor Elicit Early Pro-Apoptotic Mechanisms in Neuroblastoma Cells. J. Agric. Food. Chem. 2011, 59, 4979-4986.

 

19. Lu, T.; Hayashi, R.; DeKorver, K. A.; Lohse, A. G.; Song, Z. L.; Hsung, R. P. Synthesis of Amido-Spiro[2.2]Pentanes via Simmons-Smith Cyclopropanation of Allenamides. Organic Biomol. Chem. 2009, 9, 3331-3337 [Hot Paper].

 

18. Lu, T.; Song, Z. L.; Hsung, R. P.  A Mutually-Facial Selective Cyclopropanation of Chiral Enamides Using Dirhodium (II) Carbenoids. Org. Lett. 2008, 10, 541-544.

 

17. Song, Z. L.; Lu, T.; Hsung, P. R.; Al-Rashid, Z. F., Ko, C.; Tang, Y. Highly Stereoselective Simmons-Smith Cyclopropanations of Chiral Enamides. Angew. Chem. Int. Ed. 2007, 46, 4069-4072.

 

16. Song, Z. L.; Hsung, R. P.; Lu, T.; Lohse, A. G. Studies on a Urea-Directed Stork-Crabtree Hydrogenation. Synthesis of the C1-C9 Subunit of (+)-Zincophorin. J. Org. Chem. 2007, 72, 9722-9731.

 

15. Song, Z. L.; Hsung, P. R. A Formal Total Synthesis of (+)-Zincophorin. Observation of An Unusual Urea Directed Stork-Crabtree Hydrogenation. Org. Lett. 2007, 9, 2199-2202.

 

14. Antoline, J. E.; Hsung, R. P.; Huang, J.; Song, Z. L.; Li, G. Highly Stereoselective [4 + 3] Cycloadditions of Nitrogen-Stabilized Oxyallyl Cations with Pyrroles. An Approach to Parvineostemonine. Org. Lett. 2007, 9, 1275-1278.

 

13. Tang, Y.; Oppenheimer, J.; Song, Z. L.; You, L.; Zhang, X.; Hsung, R. P. Strategies and Approaches for Constructing 1-Oxadecalins. Tetrahedron 2006, 62, 10785-10813.

 

12. Wang, A.; Song, Z. L.; Gao, S.; Jiang, Y.; Yuan, D.; Tu, Y.; Li, N. Studies on Wagner-Meerwein Rearrangement of Benzospirocyclic β-Bromo Ketones and Application to Formal Synthesis of (±)-Colchicine Chinese. J. Org. Chem. 2007, 27, 1171-1175.

 

11. Wang, A.; Tu, Y.; Song, Z. L.; Yuan, D.; Hu, X.; Wang, S.; Gao, S.  Synthetically Useful Wagner-Meerwein Rearrangement of α-Quaternary Bromovinyl Methyl Ethers. Eur. J. Org. Chem. 2006, 2691-2694.

 

10. Song, Z. L.; Tu, Y.; Gao, S.; Jiang, Y.; Zhang, S. Studies on The Synthesis of Morphinan Alkaloid: Preparation of The Key Allylic Silyl Ether Precursor. Chinese. Chem. Lett. 2005, 1445-1447.

 

9. Gao, S.; Tu, Y.; Song, Z. L.; Wang, A.; Fan, X.; Jiang, Y. A General and Efficient Strategy for 7-Aryloctahydroindole and cis-3a-Aryloctahydroindole Alkaloids: Total Syntheses of (±)-Lycorane and (±)-Crinane. J. Org. Chem. 2005, 70, 6523-6525.

 

8. Fan, C. A.; Tu, Y. Q.; Song, Z. L.; Zhang, E.; Shi, L.; Wang, M.; Wang, B. M.; Zhang, S. Y. An Efficient Total Synthesis of (±)-Lycoramine. Org. Lett. 2004, 6, 4691-4694.

 

7. Song, Z. L.; Wang, B. M.; Tu, Y. Q.; Fan, C. A.; Zhang, S. Y. A General Efficient Strategy for cis-3a-Aryloctahydroindole Alkaloids via Stereocontrolled ZnBr2-Catalyzed Rearrangement of 2,3-Aziridino Alcohols. Org. Lett. 2003, 5, 2319-2321.

 

6. Wang, B.; Song, Z. L.; Fan, C.; Tu, Y.; Chen, W. Halogen Cation Induced Stereoselective Semipinacol-Type Rearrangement of Allylic Alcohols: A Highly Efficient Approach to α-Quaternary β-Haloketo Compounds. Synlett 2003, 1497-1499.

 

5. Fan, C.; Hu, X.; Tu, Y.; Wang, B.; Song, Z. L. Progressive Studies on the Novel Samarium-Catalyzed Diastereoselective Tandem Semipinacol Rearrangement/Tishchenko Reduction of Secondary α-Hydroxy Epoxides. Chem. Eur. J. 2003, 9, 4301-4310.

 

4. Wang, B.; Song, Z. L.; Fan, C.; Tu, Y.; Shi, Y. Lewis Acid Promoted Highly Stereoselective Rearrangement of 2,3-Aziridino Alcohols: A New Efficient Approach to β-Amino Carbonyl Compounds. Org. Lett. 2002, 4, 363-366.

 

3. Fan, C.; Wang, B.; Tu, Y.; Song, Z. L. Samarium-Catalyzed Tandem Semipinacol Rearrangement/Tishchenko Reaction of a-Hydroxy Epoxides: A Novel Approach to Highly Stereoselective Construction of 2-Quaternary 1,3-Diol Units. Angew. Chem. Int. Ed. 2001, 40, 3877-3880.

 

2. Ren, S.; Wang, F.; Dou, H.; Fan, C.; He, L.; Song, Z. L.; Xia, W.; Li, D.; Jia, Y.; Li, X.; Tu, Y. A New One-Pot Synthesis of 2-Quaternary 1,3-Diketones. Syntheses 2001, 16, 2384-2388.

 

1Fan, C.; Song, Z. L.; Tu, Y.; Wang, B. Sm(III)-Catalyzed Highly Diastereoselective Rearrangement and Reduction of α-Hydroxy Epoxides. A New Synthetic Method for Preparing 1,3-Diol Monoesters. Chinese. J. Org. Chem. 2001, 21, 1074-1080.

 

 



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