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：
电子邮箱E-mail: zhenleisong@scu.edu.cn；zhenleisong@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
1、2008年四川省卫生厅第八批学术技术带头人后备人选
2、2009，2011年度四川大学优秀青年骨干教师奖励
3、2012年四川大学引进人才（2008年进校）“优秀”奖
4、2012年“教育部新世纪优秀人才支持计划”
5、2013年“中国化学会青年化学奖”
6、2014 Asian Core Program Lectureship Award
7、2017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-Chaykovsky和Tandem 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
6、四川大学优秀青年****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(-)-Exiguolide、Nematocidal Oxylid的全合成，以及明星天然产物Bryostatins B、C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
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
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.
1．Fan, 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.
编辑：四川大学华西药学院
