1. 化學資料庫如何輔助研究工作 from organic and medicinal chemist’s point of view 簡敦誠 Tun-Cheng Chien Department of Chemistry National Taiwan Normal University Taipei, Taiwan

2. How does chemical databases assist my research work? My literature search experience –Library / journals / books / conferences / lectures –Chemical abstract –STN / SciFinder –Crossfire / Reaxys - Beilstein Our recent research work Knowledge in the cloud? 2

3. My literature search experience in prior to 1991 1993 ~ 1996 (MS / RA) –Library: CA / journals / books Comprehensive Heterocyclic Chemistry I / II / III Fieser & Fieser’s Reagents for Organic Synthesis 1~27 Reagents for Organic Synthesis Larock’s Comprehensive Organic Transformations I / II Greene's Protective Groups in Organic Synthesis –STN 1996 ~ 2006 (PhD / Postdoc) 2006 ~ now 3

4. Reaction search Substance search –known compound –purification –spectroscopic data Commercially availability 4

5. Enhance the heterolytic cleavage of N-O bond 5

6. 6 Sulfonylation of carboxamidoxime in our lab Org. Lett. 2014, 16, 892−895 Rearranged products vs non-rearranged products: O-Ts carboxamidoxime R-CN:R = alkyl aryl w/ EWG N-substituted cyanamide R-CN:R = aryl w/ EDG

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11. Tiemann Rearrangement 11 1. Tiemann, F. Ber. Dtsch. Chern. Ges. 1891, 24, 4162 2. Li, J. J. Name Reactions, 2nd Ed., 2003, Springer 3. Comprehensive Organic Name Reactions and Reagents, Wiley

12. 12 Mechanism for the Tiemann rearrangement

13. 13 Attempts to trap the nitrene intermediate X = O, benzisoxazole X = N, indazole X = O, benzoxazole X = N, benzimidazole Org. Lett. 2014, 16, 892−895

14. 14 Benzamidoximes with ortho-nucleophiles Org. Lett. 2014, 16, 892−895

15. 15 Benzamidoximes with ortho-nucleophiles

16. 16 Benzamidoximes with ortho-nucleophiles

17. Conformation of uridine and its analogs 17

18. 6-Methyluridine 18

19. 6-Methyluridine – m.p. & recrystallization 19

20. 6-Methyluridine – CD & conformation 20

21. 6-Methyluridine – crystal data 21

22. 6-Methyluridine - bioactivities 22

23. 6-Azauridine as a reference compound 23

24. 6-Azauridine as a reference compound 24

25. 6-Azauridine as a reference compound 25

26. Summary Knowledge in the cloud? vs Data / Information in the cloud? 26

27. Acknowledgments Collaborators: Kaohsiung Medical University Professor Hui-Ting Chen( 陳惠亭 ) Professor Chai-Lin Kao( 高佳麟 ) National Taiwan University Professor Ji-Wang Chern( 陳基旺 ) Professor Nei-Li Chan( 詹迺立 ) Professor Tsai-Kun Li( 李財坤 ) Financial / Technical supports: Ministry of Science and Technology National Taiwan Normal University National Applied Research Laboratories Former and current members: Methodology group Natural product group Nucleic acid group

28. Thank you for your attention!