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ZHENLEI SONG
Zhenlei Song
Professor of Medical Chemistry
West China School of Pharmacy, Sichuan University
Address: Renmin South Road 3rd Section 17#, Chengdu, Sichuan, China 610041
Phone: +86-28-85501876
Education
1996-2000  B.S., Department of Chemistry, Lanzhou University
2000-2005  Ph. D. in Organic Chemistry, Department of Chemistry, Lanzhou University (Prof. Yong-Qiang Tu)
2005-2006  Research Associate, Department of Chemistry, University of Minnesota (Prof. Richard P. Hsung)
2006-2008  Research Associate, Division of Pharmaceutical Sciences and Department of Chemistry, University of Wisconsin (Prof. Richard P. Hsung)
Awards and Honors
1. Program for New Century Excellent Talents (NCET), 2012
2. Chinese Chemical Society Young Scientist Award, 2013
3. Asian Core Program Lectureship Award, 2014
4. The National Science Fund for Outstanding Young Scholars, 2017
 
Grants
1. National Natural Science Foundation of China (20802044), 2009-2011
2. National Natural Science Foundation of China (21172150), 2012-2015
3. National Natural Science Foundation of China (21021001, 21321061), 2011-2016
4. National Natural Science Foundation of China (21290180), 2013-2017
5. National Natural Science Foundation of China (21622202), 2017-2019
6. NCET (12SCU-NCET-12-03), 2013-2015
7. RFDP (200806101091), 2009-2011
8. National Basic Research Program of China (973 Program, 2010CB833200), 2010-2014
 
Research
Research in our group centers on organosilane chemistry with a focus on the development of structurally novel and synthetically useful organosilanes. We are currently interested in a unique species: geminal bis(silane) featuring two silyl groups attached into one carbon center. We have developed a general method that leads to diverse synthesis of geminal bis(silane) building blocks and reagents. A variety of unique reactivities such as steric and electronic effects, silyl migration aptitude and bifunctionality have been discovered in more than 10 new methodologies. Several unusual chemo-, regio- and stereoselectivies have been achieved. Our investigations also demonstrate that geminal bis(silane) are very useful in natural product synthesis, as evident by total syntheses of (-)-exiguolidenematocidal oxylipid, and concise construction of B and C rings in bryostatins (please see more details in publication section).
 
 
Publication
2008-Present
57. Lu, J. Zhang, Y. B., Yang, W. Y., Guo, Q. Y. Gao, L.*; Song, Z. L.* Transformation of The B-ring to C-ring of Bryostatins by Csp3-H Amination and Z to E-isomerization Org. Lett. 2017, 19(19), 5232-5235.
 
56. Xie, H. M., Lu, J., Gui, Y. Y., Gao, L.; Song, Z. L.* (HMe2SiCH2)2: A Useful Reagent for B(C6F5)3-catalyzed Reduction/Lactonization of Keto Acids. Concise Syntheses of (-)-cis-Whisky and Cognac Lactones Synlett 2017, 28(18), 2453-2459 (SYNLETT Cluster “Silicon in Synthesis and Catalysis”)
 
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, 73(26), 3707-3713.
 
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)
 
46Li, 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.
 
Ph. D and Post-doc Works
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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Main campus address:
Wangjiang campus: section of Chengdu No. 24 Southern Yihuan Code: 610065 | 29 Jiuyanqiao WangjiangRoad, Chengdu Zip: 610064
Huaxi Campus: Chengdu, People’s SouthRoad was on the 17th Zip: 610041
Jiang’an Campus: Shuangliu County, Chengdu, Sichuan road Zip: 610207
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