宋振雷
宋振雷,男,四川大学华西药学院,教授。
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。
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年度四川大学优秀青年骨干教师奖励
3、2010年度华西药学院学生训练指导优秀教师奖
4、2011年第四届全国大学生药苑论坛创新成果项目二等奖(指导教师)
5、2011年度四川大学优秀青年骨干教师奖励
6、2018年第十四届四川省青年科技奖
研究课题
课题组专注于新型功能性有机硅化物分子的开发、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 胺醚(silane)]开展了系统的研究,并取得了以下三个方面的代表性成果:(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挑战性合成难题。(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。
迄今为止,在国际重要学术刊物Chem.Rev.,J. Am. Soc. Chem., Angew.Chem.Int.Ed.,Nat.Prod.Rep,Chem. Commun., Org.Lett.等发表论文进48篇,其中独立工作28篇,他引500多次。同行评价和推介10次,包括Synfacts5次,Organic 化学 Portal1次,《有机化学》 1次,Most Downloaded Article of Chem. Commun. 1次,X-mol Highlights2次。受邀撰稿6次,包括SYNPACTS,Chem. Commun (feature article), Tetrahedron Lett. (Digest),《化学通报》(中国化学会青年化学奖专栏),《Organic Reactions》 (The Brook Rearrangement),并于2013年获得“中国化学会青年化学奖”,2014年获得“ACP Lectureship Award”。
科研项目
1、国家自然科学基金青年基金:“硅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、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
5、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
6、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
7、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
8、国家中华人民共和国国家自然科学基金委员会重大项目:“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
发表论文
发表论文
1.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 EXOselectivity in Intermolecular Diels-Alder Reaction” J. Am. Soc. Chem. 2016,138, 1877?1883.
2.Li, H. Z.; Xie, H. M.; Zhang, Z. G.; Xu, Y. J.; Lu, J.; Gao, L.;Song, Z. L.* “Total synthesis of (-)-exiguolide via anorganosilane-based strategy” Chem. Commun 2015, 51, 8484?8487.
3.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 andApplication to Prins Cyclization” Org. Lett. 2015, 17, 1846?1849.
4.Li, L. J.; Sun, X. W.; He, Y. Y.; Gao, L.;Song, Z. L.* “TMSBr/InBr3-promoted Prins cyclization/homobromination of dienyl 乙醇 with aldehyde to construct cis-THP containing an exocyclicE-alkene” Chem. Commun 2015, 51, 14925?14928. (The 3rd most downloaded article between July-Sept. 2015, Highlighted by X-摩尔)
5. Zhang, Z. G.; Xie, H. M.; Li, H. Z.; Gao, L.;Song, Z. L.* “Total Synthesis of (?)-Exiguolide” Org. Lett. 2015, 17, 4706?4709.
6.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, 15546?15549. (Highlighted by X-摩尔)
7. 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, 1466?1473. (Invited Digest Article)
8.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 EXOCyclization/Rearrangement of 3,3-Bis(silyl) Enol Ester with a Tethered Acetal” Org. Lett. 2015, 17, 1553?1556
9.Wu, Y.; Gao, L.*;Song, Z. L.* “Recent Advances in 硅Stereogenic Chiral Organosilanes” 化学, 2015, 78, 676?680. (Invited Chinese Chemical Society Young Scientist Award Article)
10.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 硅" Org. Bio摩尔 Chem., 2014, 12, 3021?3025.
11.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 胺醚(silyl) N?Acyl Pyridinium"Org. Lett. 2014, 16, 1880?1883. [Highlight in SYNFACTS, 2014, 10, 0743]
12.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 锂: A Useful Scaffold forSyn-Addition to Aldehydes and Ketones" Org. Lett. 2014, 16, 1084?1087 [Highlight in SYNFACTS, 2014, 10, 0522.].
13.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, 984?987.
14.Gao, L.; Lu, J.;Song, Z. L.* "Recent Efforts to Construct The B-Ring of Bryostatins" Chem. Commun. 2013, 49, 10211?10220. (Invited Feature Article)
15.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 胺醚(silane)" Chem. Commun. 2013, 49, 8961?8963.
16.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 胺醚(silane). Concise Synthesis of Nematocidal Oxylipid" Org. Lett. 2013, 15, 1068?1071.
17.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 化学" Org. Lett. 2013, 15, 1104?1107.
18.Sun, X. W.;Song, Z. L.*; Li, H. Z.; Sun, C. Z. "[1,4]-S- to O-Silyl Migration: Multicomponent Synthesis of a-Thioketonesthrough Chemoselective Transformation of Esters to Ketones with Organolithium Reagents" Chem. Eur. J. 2013, 19, 17589?17594.
19.Gao, L.; Zhang, Y. B.;Song, Z. L.* "Exploration of Versatile Geminal 胺醚(silane) 化学" Synlett 2013, 24, 139?144. (Invited SYNPACT Article)
20.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, 5367?5370. [Highlight in Org. Chem. Highlights 2013, January 14; Chin. J. Org. Chem. 2012, 32, 1553.]
21.Gao, L.; Lin, X. L.; Lei, J.;Song, Z. L.*; Lin Z. "Bissilyl Enal: A Useful Linchpin for Synthesis of Functionalized Vinylsilane 物种 by Anion Relay 化学" Org. Lett. 2012, 14, 158?161.
22.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 胺醚(silane) 物种" Org. Lett. 2012, 14, 1094?1097. [Highlight in SYNFACTS, 2012, 8, 0544.]
23.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.
24.Song, Z. L.; Fan, C. A.; Tu, Y. Q. "Semipinacol Rearrangement in Natural Product Synthesis" Chem. Rev. 2011, 111, 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, 1440?1443. [Highlight in SYNFACTS, 2011 (6), 0660.]
26.Wang, C.; Gan, Z. B.; Lu, J.; Wu, X.;Song, Z. L.* "A highly stereoselective approach to tetrasubstituted (E)-b-hydroxy silyl enol ethers by addition of aryl-substituted oxiranyl anions to acylsilanes" Tetrahedron Lett. 2011, 52, 2462?2464.
27.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, 306?309.
28.Song, Z. L.*;Lei, Z; G, Lu.; 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, 5299?5302. [Highlight in SYNFACTS, 2011 (2), 0194.]
29.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.
参考资料
导师介绍 - 宋振雷课题组.四川大学.2022-01-19