張彥誠教授


e-mail: ncchang@mail.nsysu.edu.tw

 

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教授(1990)
副教授(1983)

美國哈佛大學博士後研究(1982)

美國德州大學奧斯汀分校博士(1982)

國立成功大學化學系學士(1972)

獎勵與榮譽:

民國七十八年、七十九年國科會優等研究獎

民國七十八年中山大學傑出研究獎


研究興趣

1. 有機新合成方法

2. 有機光電材料

3. 藥物合成

4. 天然物合成

    我們發現以 a-sulfonyl acetamides 與 Michael accepters 可以進行 [3+3]或[3+2]環化反應,分別生成 glutarimides 及 pyroglutarimides。利用此二類生成物本身所具有的特性,我們開發出新的途徑來建構具有不同取代基的 indolizidine、quinolizidine、 pyrrolizidine、quinolone、isoquinolone 及 indole的基本骨架。這些結果進一步的應用於藥物、天然物以及光電材料的合成。


代表著作

1.        S.-L. Hsieh, C.-T. Chiu, N.-C. Chang, A formal total synthesis of (±)-9-isocyanopupukeanane, J. Org. Chem. 1989, 54, 3820-3823.

2.        N.-C. Chang, H.-M. Day, W.-F. Lu, Total synthesis of (±)-dimethyl secologanoside O-methyl ether, J. Org. Chem. 1989, 54, 4083-4088.

3.        L.-F. Hsu, C.-P. Chang, M.-C. Li, N.-C. Chang, Bicyclo[3.2.1]octenones as building blocks in natural products synthesis. 1. Formal synthesis of (±)-mussaenoside and (±)-8-epiloganin aglycons, J. Org. Chem. 1993, 58, 4756-4757.

4.        C.-P. Chang, L.-F. Hsu, N.-C. Chang, Bicyclo[3.2.1]octenones as Building Blocks in Natural Products Synthesis. 2. Formal Synthesis of (±)-Verbenalol, J. Org. Chem. 1994, 59, 1898-1899.

5.        N.-C. Chang, C.-K. Chang, Total Synthesis of (±)-2-Pupukeanone, J. Org. Chem. 1996, 61, 4967-4970.

6.        M.-Y. Chang, C.-P. Chang, W.-K. Yin, N.-C. Chang, Total Synthesis of (±)-Sarracenin, J. Org. Chem. 1997, 62, 641-644.

7.        Y.-L Chen, T.-C. Wang, K.-C. Fang, N.-C. Chang, C.-C. Tzeng, Synthesis of Certain Quinolin-2(1H)-one α-Methylene-γ-butyrol actones as Potential Anti- platelet Agents, Heterocycles 1999, 50, 453-462.

8.        M.-Y. Chang, N.-C. Chang, Formal Synthesis of (±)-Mitsugashiwalactone and (±)-Isodihydronepetalactone from Norborn-5-en-2-one Involving Shapiro Reaction, J. Chin. Chem. Soc. 1999, 46, 41.

9.        H.-M. Tai, M.-Y. Chang, A.-Y. Lee, N. C. Chang, A Versatile Diquinane from Fulvene as a Building Block in Natural Product Synthesis. 1. A Facile Synthesis of the Iridoids-Loganin and Sarracenin, J. Org. Chem. 1999, 64, 659.

10.    M.-Y. Chang, C.-H. Lin, A.-Y. Lee, H.-M. Tai, N.-C. Chang, Total Synthesis of (±)-Boschnialactome and (±)-Tetrahydroanhydrodesoxy-aucubigenin, J. Chin. Chem. Soc. 1999, 46, 205.

11.    A.-Y. Lee, M.-Y. Chang, N.-C. Chang, Total Synthesis of (±)-Pedicularis-lactone and (±)-Ningpogenin, Heterocycles 1999, 51, 295-302.

12.    Y.-L. Chen, T.-C. Wang, N.-C. Chang, C.-C. Tzeng, Geiparvarin Analogues: Synthesis and Anticancer Evaluation of α-Methylene-γ-butyrolactone Bearing Coumarins, Helv. Chim. Acta. 1999, 82, 191-197.

13.    M.-Y. Chang, C.-H. Lin, N.-C. Chang, Synthesis of Acetal Dioxa-Cage Compounds via Intramolecular Acetalization, J. Chin. Chem. Soc. 1999, 46, 591.

14.    A.-Y. Lee,M.-Y. Chang, H.-M. Tai, N.-C. Chang, Total Synthesis of (±)-Iridolactone, J. Chin. Chem. Soc. 1999, 46, 937.

15.    M.-Y. Chang, B.-R. Chang, H.-M. Tai, N.-C. Chang, An Efficient Synthesis of N-benzyl-3-sulfonyl Glutarimides. Formal Synthesis of The Aromatase Inhibitor AG-1, Tetrahedron Lett. 2000, 41, 10273-10276.

16.    H.-M. Tai, C.-C. Yang, M.-L. Yeh, N.-C. Chang, Synthesis of Iridoid Monoterpenes and Prostaglandines, via Photochemical Rearrangement of Bicyclo[2.2.1]hept-5-en-2-one, J. Chin. Chem. Soc. 2001, 48, 901-905.

17.    M.-Y. Chang, S.-T. Chen, N.-C. Chang, Synthesis of 2,6-Dioxatetracyclo [6.3.0.01,10.07,8]-undecane and 2,7,12-Trioxatetracyclo[6.3.1.04,11.05,9]dodecane, J. Chin. Chem. Soc. 2001, 48, 1153-1156.

18.    M.-Y. Chang, B.-R. Chang, C.-H. Chang, S.-T. Chen, N.-C. Chang, Formal Synthesis of (±)-Isodihydronepetalactone, J. Chin. Chem. Soc. 2002, 49, 233-237.

19.    M.-Y. Chang, C.-H. Chang, S.-T. Chen, N.-C. Chang, A Synthesis of Thalidomide, J. Chin. Chem. Soc. 2002, 49, 383-385.

20.    M.-Y. Chang, J. Y.-C. Lin, S.-T. Chen, N.-C. Chang, 1,8-diazabicyclo [5.4.0] undec-7-ene: A remarkable base in the debromination of 4-or 5-substituted N-benzyl alpha-bromo-alpha-p-toluenesulfonylglutarimide, J. Chin. Chem. Soc. 2002, 49, 1015-1024.

21.    M.-Y. Chang, J. Y.-C. Lin, S.-T. Chen*, N.-C. Chang*, Synthetic study of 4-substituted piperidine ring in elarofiban, RWJ-50042, tirofiban and paroxetine, J. Chin. Chem. Soc. 2002, 49, 1079-1088.

22.    C.-C. Huang, B.-R. Chang, N.-C. Chang*, An Efficient Synthesis of γ-Substituted α,βz-Unsaturated δ-Lactams. Formal Synthesis of (±)-Protoemetinol , Tetrahedron Lett. 2002, 43, 2721-2723 .

23.    B.-R. Chang, C.-Y. Chen, N.-C. Chang*, Regioselective Reduction of N-Alkyl-3-sulfonyl Glutarimides. Synthesis of 5,6-Dihydro-3-tosylpyridine - 2-ones, Tetrahedron Lett. 2002, 43, 3233-3235.

24.    R.-T. Hsu, L.-M. Cheng, N.-C. Chang*, H.-M. Tai*, Regioselective Reduction of 3-Sulfonyl Glutarimides to 3,4-Dihydro-5-sulfonylpyridin-2-ones. Formal Synthesis of Indolizidine, 8a-epi-Dendroprimine, J. Org. Chem. 2002, 67, 5044-5047.

25.    M.-Y. Chang, S.-T. Chen*, N.-C. Chang*, New synthesis of 3-aryl-N-n- propyl-piperidines, Tetrahedron 2002, 58, 3623-3628.

26.    M.-Y. Chang, S.-T. Chen*, N.-C. Chang*, Reaction of Different -Sulfonyl Acetamides with Methyl Acrylate, Tetrahedron 2002, 58, 5075-5080.

27.    M.-Y. Chang, S.-T. Chen*, N.-C. Chang*, An efficient synthesis of N-alkyl-4- substituted 3H-pyridine-2,6-dione. Synthesis of isoguvacine and MDL-11,939, Heterocycles 2002, 57, 2321-2334.

28.    M.-Y. Chang, S.-T. Chen*, N.-C. Chang*, Regioselective reduction of N-alkyl-3-sulfonyl- glutarimide. Formal synthesis of 1,2,3,4,6,7,12,12b-octa- hydroindolo[2,3-a]quinolizine and homobaclofen, Heterocycles 2003, 60, 99-112.

29.    M.-Y. Chang, P.-P. Sun, , S.-T. Chen*, N.-C. Chang*, Synthesis of (±) Rolipram, Heterocycles 2003, 60, 1865-1872.

30.    M.-Y. Chang, K.-G. Lin, S.-T. Chen*, N.-C. Chang*, Solid phase synthesis of 3-Toluenesulfonylglutarimides, J. Chin. Chem. Soc. 2003, 50, 795-797.

31.    M.-Y. Chang, S.-T. Chen*, N.-C. Chang*, A Synthesis of Racemic Thalidomide, Syn. Commun. 2003, 33, 1375-1382.

32.    M.-Y. Chang, S.-T. Chen*, N.-C Chang*, Formal Synthesis of Anisomycin, Heterocycles 2003, 60, 1203-1209.

33.    P.-P. Sun, M.-Y. Chang, M.-Y. Chiang, N.-C Chang*, A Facile Route to Polysubstituted N-Benzyl Pyroglutamates, Org. Lett. 2003, 5, 1761-1763.

34.    M.-Y. Chang, P.-P. Sun, , S.-T. Chen, N.-C. Chang, A Facile Synthesis of 3-Aryl Pyroglutamic Acid. Facile Synthesis of Baclofen and Chlorpheg, Tetrahedron Lett. 2003, 44, 5271-5273.

35.    C.-H. Lin, M.-R. Tsai, Y.-S. Wang, N.-C. Chang*, An Efficient Approach to 3,4-Disubstituted pyridin-2-ones. Formal Synthesis of Mappicine Ketone, J. Org. Chem. 2003, 68, 5688-5691.

36.    M.-Y. Chang, C.-Y. Chen, S.-T. Chen*, N.-C. Chang*, Synthesis of fused bicyclic glutarimides, Tetrahedron, 2003, 59, 7547.

37.    C.-Y. Chen,. M.-Y. Chang, R.-T. Hsu, S.-T. Chen, N.-C. Chang*, One-pot facile conversion of Baylis-Hillman adduct into N-alkyl 3-(E)-alkylidene-5-substituted sulfonylpiperidine-2,6-dione. Formal synthesis of tacamonine, Tetrahedron Lett. 2003, 44, 8627-8630.

38.    C.-Y. Chen, B.-R. Chang, M.-R. Tsai, M.-Y. Chang, N.-C. Chang*, Regioselective reduction of N-alkyl-3-sulfonyl glutarimides to d-lactams. Formal synthesis of (±)-paroxetine and (±)-tacamonine, Tetrahedron, 2003, 59, 9383-9387.

39.    M.-Y. Chang, C.-H. Lin, N.-C. Chang*, Formal synthesis of (±)-udoteatrial hydrate. Tetrahedron, 2004, 60, 1581-1585.

40.    M.-Y. Chang, C.-Y. Chen, M..-R. Tasi, T.-W. Tseng, N.-C. Chang*, New Synthesis and Application of 3-Substituted Prolinols. Synthesis, 2004, 840-846.

41.    M.-R. Tsai, P.-P. Sun, M.-Y. Chang, N.-C. Chang*, New Approach to N- substituted-1,2,3,6-tetrahydro-pyridine-4-carbaldehyde, a Precursor for Synthesizing Aricept®, Isoguvacine, and Deethylibophyllidine, J. Chin. Chem. Soc. 2004, 51,613-617.

42.    M.-Y. Chang, R.-T. Hsu, T.-W. Tseng, P.-P. Sun, N.-C. Chang*, Synthesis of Psudoheliotridane via Formal [3+2] Annulation and Ring-closing Metathesis, Tetrahedron 2004, 60, 5545-5550.

43.    B.-F. Chen, M.-R. Tasi, C.-Y. Yang, J.-K. Chang, N. -C. Chang*, A versatile approach to 6-substituted-5-methoxy-d-lactam framework and application to the formal synthesis of (±)-homopumiliotoxin 223G, Tetrahedron 2004, 60, 10223-10231.

44.    M.-R. Tasi, T.-C. Hung, B.-F. Chen, C.-C. Cheng, N.-C. Chang*, Synthesis of 3,4-dihydrobenzo[g]isoquinoline-1(2H)-ones and 3,4-dihydroisoquinoline-1(2H) -ones skeleton via intramolecular electrophilic cyclization, Tetrahedron 2004, 60, 10637-10644.

45.    M.-Y. Chang, C.-Y. Chen, W.-S. Chung, M.-R. Tasi, N.-C. Chang*, An easy ABDABCD strategy to indolo[2,3-a]quinolizin-4-one. Synthesis of deplancheine and yohimbane, Tetrahedron 2005, 61, 585-591.

46.    M.-Y. Chang, H.-M. Tai, C.-H. Lin, N.-C. Chang*, Synthesis of Lupinine, Heterocycles 2005, 65, 395-402.

47.    M.-R. Tasi, B.-F. Chen, C.-C. Cheng, N. -C. Chang*, A Novel and Highly Regioselective Approach to 5-Methoxy-6-substituted-3-sulfonyl-d-enlactams from 5-Methoxy-3-sulfonyl glutarimide. Synthesis of cis-2-Substituted-3- piperidinols, J. Org. Chem. 2005, 70, 1780-1785.

48.    C.-H. Wang, O.-Y.-H. Tai, Y. Wang, T.-H. Tsai, N. -C. Chang, Non-quadratic Intensity Dependence of Two-photon Absorption Induced Fluorescence of Organic Chromophores in Solution, J. Chem. Phys. 2005, 122, 084509.

49.    R.-T. Hsu, N.-C. Chang, M.-Y. Chang, Formal Synthesis of (±)-Trachelanthamidine via Base-induced Formal [3+2] Annulation and Intramolecular Cyclization, J. Chin. Chem. Soc. 2006, 53, 945-954.

50.    M. -Y. Chang, R. -T. Hsu, C. -Y. Lin, B. -F. Chen, S. -T. Lin, N. -C. Chang, Formal Synthesis of (±)-Hop Ether, (±)-Isoboonein, and (±)-Iridomyrmecin, Heterocycles 2006, 68, 271-282.

51.    H.-W. Chen, R.-T. Hsu, M.-Y. Chang, and N.-C. Chang*, Efficient Synthesis of Fused Bicyclic Glutarimides. Its Application to (±)-Alloyohimbane and Louisianin D, Org. Lett. 2006, 8, 3033-3035.

52.    T.-H. Tsai, W.-H. Chung, J.-K. Chang, R.-T. Hsu, N.-C. Chang, A facile approach to polysubstituted 2-pyridones. Application to the synthesis of 3,4-disubstituted isoquinolinone and total synthesis of oxyisoterihanine, Tetrahedron 2007, 63, 9825-9835.

53.    M.-Y. Chang, C.-Y. Lin, P.-P. Sun, N.-C. Chang, Total Synthesis of (±)-Boonein, J. Chin. Chem. Soc. 2007, 54, 239-243.

54.    C.-C. Huang, N.-C. Chang, New Approach to 2-Quinolinones, Org. Lett. 2008, 10, 673-676.

55.    J.-K. Chang, N.-C. Chang, Total Synthesis of (±)-Gusanlung D, Tetrahedron 2008, 64, 3483-3487.

56.    Y.-S. Wang, N.-C. Chang, C.-H. Lin, H.-M. Tai, Efficient Synthesis of 4,5-Disubstituted-3-toluenesulfonyl Glutarimides. Application to the Formal Synthesis of Mappicine Ketone, J. Chin. Chem. Soc. 2008, 55, 431-434.

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