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E-mail

080686@mail.fju.edu.tw

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³Õ¤h«á¬ã¨s­û(2010)        ¥xÆW¤j¾ÇÃľǩÒ

³Õ¤h«á¬ã¨s­û(2009)        ¬ü°êNorthwestern University

³Õ¤h«á¬ã¨s­û(2008)        ¥[®³¤jUniversity of Alberta

¤Æ¾Ç³Õ¤h(2007)     °ê¥ß¥xÆW¤j¾Ç

³X°Ý³Õ¤h¥Í(2006) ¼w°êUniversity of Münster DAAD

¬ã¨s§U²z(2002)     ¤¤¥¡¬ã¨s°|¥Í¤Æ©Ò

§U±Ð(2000)     ¥xÆW¤j¾Ç¤Æ¾Ç¨t

¤Æ¾ÇºÓ¤h(1999)     °ê¥ß¥xÆW¤j¾Ç

¤Æ¾Ç¾Ç¤h(1997)     °ê¥ß¤¤¿³¤j¾Ç

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¥»¹êÅç«Ç¬ã¨s¥DÃD¬O¥H¦³¾÷¦X¦¨ (organic synthesis) ªº¤èªk¡A¨Ó»s³Æ¨ã¦³¥Íª«©Î¬O¨ãÃĪ«¬¡©Êªº¦³¾÷¤À¤l¡C¥]§t¤U­±´X­Ó¥DÃD:

(1)    ¤ÑµMª«¥þ¦X¦¨ (natural product synthesis)¡A§Q¥Î·sªº¦X¦¨¤èªk»s³Æ¤ÑµMª«¡A¨Ò¦p¡GSCH 71450 (¤@ºØªvÀø¹L°Êªº°t¤è¥ÎÃÄ);  ribulose-5-phosphate»Pxylulose-5-phosphate (¤HÅ饳ÁÞÁC»Ä¥NÁ³~®|ªº­«­n¤¤¶¡¤Æ¦Xª«)¡C

(2)    ÃĪ«¦X¦¨ (new synthesis of drugs)¡A§Q¥Î·s¶}µoªº¦X¦¨¤èªk¾Ç¨Ó»s³Æ¤wª¾ÃĪ«¡A©Î¬O¨ã¦³ÃĪ«¬¡©Êªº¦³¾÷¤Æ¦Xª«¡A¨Ò¦p¡G Telbivudine (L-dT¡ASEBIVOTM¡ANovartis¡A³ß¥²ºÖ¡A¿ÕµØ¡A·s¤@¥NªvÀøB«¬¨xª¢ªºÃĪ«);  Rolipram (PDE4 inhibitor¡AÁC»ÄÂùà­酶4«¬§í¨î¾¯¡A§Ü¼~Æ{»P§Üªü¯÷®üÀq¯gÀø®Ä);  Phenylpiracetam (Phenotropil¡A§Ü¼~Æ{»P¥¢´¼¯gÃĪ«);  Phenylpiracetam hydrazide (fonturacetam hydrazide, §ÜÅöíwÀø®Ä)

(3)    ¶}µo¦X¦¨¤èªk¾Ç (synthetic methodologies)¡A¨Ò¦p:

(2-1) §Q¥Îæó°ò²¾¦ì (carbonyl translocation) ªº¦X¦¨¤èªk¾Ç¡A±N«K©yªºÁÞ­ì®Æ (carbohydrate raw material)¡AÂà´«¬°­«­n©ù¶Q¥Bµ}¦³ªº¦X¦¨«Øºc²Õ¤¸¡AÁÞÃþ¤À¤l¡A©Î¬O¨ã¥Íª«¬¡©Ê¤À¤l¡A¦p: 2-¥h®ñ-L-®ÖÁÞ (2-deoxy-L-ribose)¡A3-¥h®ñ-L-ªG¿} (3-deoxy-L-fructose)¡A®Öà¬ÁÞ (D-ribulose)¡A¤ìà¬ÁÞ (D-xylulose)¡A2-¥h®ñ-L-®ÖÁÞ®Ö苷 (L-deoxyribonucleoside)

(2-2) §Q¥Î¤A²m¦Û¥Ñ°ò (vinyl radical) ¶i¦æipso¦XÀô¤ÏÀ³ (ipso cyclization) ¨Ó¦X¦¨¤ÑµMª«©Î¬OÃĪ«ªºµ²ºc°©¬[¡A¦p: b-­f°ò-g-¤ºñQÓi (b-aryl-g-lactam)¡A¤£¹¡©M-b-­f°ò-g-¤ºñQÓi (unsaturated-b-aryl-g-lactam)¡C

(4)    ±±¨îªº¬¡©Ê¦Û¥Ñ°ò»E¦X¤ÏÀ³ (controlled living radical polymerization)¡A¨Ò¦p: ³]­p¦X¦¨ÁÞÃþ»E¦Xª«³æÅé¤W§t¦³»PÀù²Ó­Mªí­±¤W¦³ÃöªºÁÞÃþ¤À¤l (tumor-associated carbohydrate antigens)¡A¨Ã§Q¥Î±±¨îªº¬¡©Ê¦Û¥Ñ°ò»E¦X¡A¨Ó»s³Æ¨ã¦³Àù¯g¬ÛÃö§Ü­ìÁÞ¤À¤l¡A¦pTnªºÁÞÃþ»E¦Xª«¡A§Æ±æ¯à¼ÒÀÀ¦X¦¨ÁÞÃþ§ÜÀù¬Ì­] (anticancer vaccines)¡C

(5)    ³]­p»P¦X¦¨¦³¾÷ÃĪ«¤À¤l (design and synthesis of drug-like molecules)¡A¨Ò¦p:³]­p¦X¦¨§ä¥X¨ã°ª«×¿ï¾Ü©Ê¾~¤ùÃþ¨üÅé (opioid receptor) ªº«ú§Ü¾¯ (antagonists)¡A¥Hµo®i·s«¬ªº¤îµh¾¯ (pain killers)¡C

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Independent research (¿W¥ß¬ã¨s¤u§@¡A°ß¤@³q°T§@ªÌ)
21.   New Synthesis of £]-Aryl-GABA Drugs

        Pei-Ling Wang (¤ý¨KÕæ), Yi-Xuan Chan (¸âÖöÞ±), Che-Chien Chang*

Tetrahedron 2023, 146, 133648.

20.   From a Carbohydrate Raw Material to an Important Building Block: Cost-efficient Conversion of D-Fructose into 2-Deoxy-L-ribose

Ya-Han Hsu (³\¶®²[), Che-Chien Chang*

J. Org. Chem. 2022, 87, 13308-13314.

19   Cascade Vinyl Radical Ipso-Cyclization Reactions and the Formation of a,b-Unsaturated-b-aryl-g-lactams from N-Propargyl Benzamides

       Chih-Hao Luo (Àd­P»¨), Pei-Ling Wang (¤ý¨KÕæ), Che-Chien Chang*

       J. Org. Chem. 2021, 86, 15033-15044.

18.  Conversion of a Readily Available Carbohydrate Raw Material into a Rare L-Deoxyhexose

       Ya-Han Hsu (³\¶®²[), Che-Chien Chang*

       Tetrahedron Lett. 2021, 63, 152718.

17. Design and Synthesis of Trivalent Tn Glycoconjugate Polymers by Nitroxide-Mediated Polymerization

Si-Xian Liu(¼B«äùÜ), Yun-Tzu Tsai (½²ªå·O), Yu-Tung Lin (ªL¬ê§Í), Jia-Yue Li(§õ¨ÎéÄ), and Che-Chien Chang*

Tetrahedron 2019, 75, 130776.

16.  Synthesis of L-Deoxyribonucleosides from D-Ribose.

Wei-Syun Song (§º­³¾±), Si-Xian Liu(¼B«äùÜ), and Che-Chien Chang*

       J. Org. Chem. 2018, 83, 14923-14932. 

15.  Chemical Synthesis of Ketopentose-5-phosphates.

Wei-Chih Wei (ÃQÞ³§Ó) and Che-Chien Chang*

Eur. J. Org. Chem. 2017, 3033-3040. 

Àò¿ï¬°·í´Áªº´Á¥Z«Ê­±¬G¨Æ: http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201700685/full

14.  Synthesis of 3-Deoxy-L-ketohexoses Through Group Transfer.

Tai-Ni Lu (¿c©§©g) and Che-Chien Chang*

J. Org. Chem. 2016, 81, 469-475. 

13.  Radical Cyclization Followed by the Fragmentation of Carbonyl Compounds: Effect of an alpha-Benzoyl Group.

Li-An Chien(²Ày¦w) and Che-Chien Chang*

J. Org. Chem. 2015, 80, 11294-11301.

12.  Chemical synthesis of 1-deoxy-L-fructose and L-sorbose through carbonyl translocation.

Hsin-Pei Wu(§dªY»_), Nai-Yun Hsu(³\¤D¤ª), Tai-Ni Lu (¿c©§©g), and Che-Chien Chang*

Eur. J. Org. Chem. 2015, 378-382.

11.  Synthetic mimics of carbohydrate-based anticancer vaccines: preparation of carbohydrate polymers bearing unimolecular trivalent carbohydrate ligands

by controlled living radical polymerization.

Teng-Yuan Kuo(³¢Äˤ¸), Li-An Chien(²Ày¦w), Ya-Chi Chang(±i¨Èºö), Shuang-Yu Liou(¼B¬Û§±), and Che-Chien Chang*

RSC Adv., 2014, 4, 47066-47075.

10.  The absolute stereochemical assignment of SCH 71450, a selective dopamine D4 receptor antagonist, through the enantioselective epimer synthesis.

Hsin-Pei Wu(§dªY»_), Tai-Ni Lu (¿c©§©g), Nai-Yun Hsu(³\¤D¤ª), and Che-Chien Chang*

Eur. J. Org. Chem. 2013, 2898-2905.

9.  A unique synthetic method to convert a D-sugar into 2-deoxy-L-ribitol through carbonyl translocation.

Nai-Yun Hsu(³\¤D¤ª) and Che-Chien Chang*

Eur. J. Org. Chem. 2013, 658-661.

 

 

Selected Invited Lectures (­«­n·|ijÁܽкtÁ¿)

 

Dec 12, 2019, Session 78-3, The 18th Asian Chemical Congress (18ACC), Taipei, Taiwan

¡§Formal Total Synthesis of Telbivudine (L-dT)¡¨

Nov 22, 2018, SIL-12A, The 13th International Symposium on Organic Reactions (ISOR-13), Hsinchu, Taiwan.

¡§Synthesis of L-Deoxyribonucleosides from D-Ribose¡¨

Apr 22, 2016, SIL-2B, The 12th International Symposium on Organic Reactions (ISOR-12), Kyoto, Japan.

¡§Carbonyl Translocation in the Synthesis of Deoxysugars¡¨

May 01, 2015, ¬ì§Þ³¡¦³¾÷¦X¦¨¤p²Õ¬ã°Q·|, ¤¤¿³¤j¾Ç´f»^ªL³õ

¡§Radicals in the Synthesis of Deoxysugars and Glycopolymers¡¨

Dec 04, 2010, ¤¤°ê¤Æ¾Ç·|¦~·|, ¥xÆW¤j¾Ç®ú¤j¨¹Á¿°ó

¡§Antagonism of Dihydropyridines Toward Voltage Dependent Ca2+ Channels, Cav1.3 and Cav1.2¡¨

 

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Before FJCU

 

Postdoc work (Canada and United States)

8.     Farzad Malihi, Derrick. L. J. Clive,* Che-Chien Chang and Minaruzzaman, Synthetic studies on CP-225,917 and CP-263,114: Access to advanced tetracyclic systems by intramolecular conjugate displacement and [2,3]-Wittig rearrangement, J. Org. Chem. 2013, 78, 996-1013.  (with Clive)

7.     Che-Chien Chang, Song Cao, Soosung Kang, Li Kai, Xinyong Tian, Prativa Pandey, Sara Fernandez Dunne, Chi-Hao Luan, D. James Surmeier*, Richard B. Silverman*, Antagonism of 4-substituted 1,4-dihydropyridine-3,5-dicarboxylates toward voltage-dependent L-type Ca2+ channels Cav1.3 and Cav1.2, Bioorg. Med. Chem. 2010, 18, 3147-3158. (with Silverman)

 

PhD work (Taiwan and Germany)

6.   Che-Chien Chang, Yu-Hsien Kuo and Yeun-Min Tsai*, The synthesis of carbohydrate-derived acylsilanes and their intramolecular free radical cyclization with the formation of polyoxygenated cyclopentanes, Tetrahedron Lett. 2009, 50, 3805-3808.   (with Tsai)

5.   Che-Chien Chang, Kai O. Siegenthaler and Armido Studer*, A new sterically highly hindered 7-membered cyclic nitroxide for the controlled living radical polymerization, Helv. Chim. Acta, 2006, 89, 2200-2210. (with Studer)

4.     Che-Chien Chang and Armido Studer*, Acceleration of the styryl-TEMPO mediated controlled radical styrene-polymerization by addition of an efficient alkoxyamine, Macromolecules, 2006, 39, 4062-4068.     (with Studer)

 

Before PhD

3.     Wen-Bin Yang, Yu-ing Yang, Yu-Feng Gu, Shwu-Huey Wang, Che-Chien Chang, and Chun-Hung Lin*, Stereochemistry in the synthesis and reaction of exo-glycals, J. Org. Chem. 2002, 67, 3773-3782.

2.     Chuan-Fa Chang, Wen-Bin Yang, Che-Chien Chang and Chun-Hung Lin*, Inter- and intramolecular alcohol additions to exo-glycals, Tetrahedron Lett. 2002, 43, 6515-6519.

1.     Wen-Bin Yang, Chung-Yi Wu, Che-Chien Chang, Shwu-Huey Wang, Chin-Fen Teo and Chun-Hung Lin*, Facile synthesis of conjugated exo-glycals, Tetrahedron lett. 2001, 42, 6907-6910.