Facebook Instagram

/ Members /

Faculty
Contract-employed Professor
Adjunct Professor
Emeritus Chair Professor
Retired Professor
Staff

Nein-Chen Chang

/ Education /

Ph.D. in Chemistry, University of Texas at Austin, USA (1982)
B.S. in Chemistry, National Cheng Kung University (1972)

/ Experience /

Professor, Department of Chemistry, National Sun Yat-sen University (1990)
Associate Professor, Department of Chemistry, National Sun Yat-Sen University (1983)
Postdoctoral Researcher, Harvard University, USA (1982)
National Science Council Excellence in Research Award (1989, 1990)
National Sun Yat-sen University Outstanding Research Award (1989)
1. New synthetic methods in organic chemistry
2. Organic optoelectronic materials
3. Drug synthesis
4. Natural product synthesis
We discovered that using α-sulfonyl acetamides with Michael acceptors can undergo [3+3] or [3+2] cyclization reactions, forming glutarimides and pyroglutarimides, respectively. Utilizing the inherent properties of these compounds, we have developed new pathways to construct the basic skeletons of indolizidines, quinolizidines, pyrrolizidines, quinolones, isoquinolones, and indoles. These results have further applications in the synthesis of pharmaceuticals, natural products, and optoelectronic materials.

/ Works /

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,β�-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 ABD→ABCD 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.

/ Patents /