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wchiou@dragon.nchu.edu.tw

Tel

04-22840411#420

有機化學

Organic Chemistry

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u  Ph. D. State University of New York at Stony Brook (2005)

u  M.S. National Tsing Hua University (1995)

u  B. S. National Tsing Hua University (1993)

 

l 副教務長兼課務組組長，Deputy dean in the office of academic affairs / Adjunct director at the curriculum section (2018-presernt).

l 課務組組長，Adjunct director at the curriculum section (2015-2018).

l Professor, National Chung-Hsing University (2015-Present)

l Associate Professor, National Chung-Hsing University (2011-2015)

l Assistant Professor, National Chung-Hsing University (2006-2011)

l Postdoctoral Associate, OSI Pharmaceutical Inc., New York, US (2006)

l Postdoctoral Associate, State University of New York at Stony Brook (2005)

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My research interests focus on syntheses towards natural products with medicinal bioactivity or structure interests, especially through a domino design which allows rapid construction of complex molecules in an economic way. We have successfully developed the Rh-catalyzed hydroformylation double cyclization strategy for the synthesis of natural alkaloids. As a synthetic research group, our group continues to develop novel synthetic strategy for natural product synthesis, novel organocatalysts or structures for chiral syntheses, and mechanistic studies using computational chemistry for selectivity issues in our research. Currently, several target molecules have been achieved according to the strategies, please see the following publications for more details.

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(A). Reaserach Articles:

1.    Jui-Lin Wu (吳瑞麟) and Wen-Hua Chiou (邱文華)* “Diastereocontrolled Formal Syntheses of (±)-Lepadiformines A, B and C and the Divergent Synthesis of 2-epi-Lepadiformine C through Unexpected Double Consecutive Epimerizations" J. Org. Chem. 2020, 85, 9051-9063. https://dx.doi.org/10.1021/acs.joc.0c00964

2.    Wen-Hua Chiou (邱文華)*, Kuo-Hsun Hsu (徐國訓) and Wen-Wei Huang (黃文葦) “Rh-Catalyzed Hydroformylation-Initiated Bicyclization: Construction of Azabicyclic Systems" ACS Omega. 2020, 5, 3190-3717-3724. https://dx.doi.org/10.1021/acsomega.9b04400

3.    Jui-Chi Tsai (蔡汭祁), Yi-Huei Lin (林益暉), Guei-Tang Chen (陳貴棠), Yu-Kai Gao (高煜凱), Yu-Che Tseng (曾于哲), Chien-Lun Kao (高健倫) and Wen-Hua Chiou (邱文華)* “Rhodium-Catalyzed Domino Hydroformylation/Double-Cyclization Reactions of Arylacetlyenecarboxamides: Diastereoselectivity Studies and Application in the Synthesis of 1-Azabicyclo[x.y.0]alkane" Chem. Asian J. 2018, 13, 3190-3197. https://doi.org/10.1002/asia.201801193

4.    Yu-Han G. Teng, Chih-Wei Chien, Wen-Hua Chiou, (邱文華) Tadashi Honda and Iwao Ojima* “Construction of Fused Tropone Systems Through Intramolecular Rh(I)-Catalyzed Carbonylative [2+2+2+1] Cycloaddition of Triynes" Front. Chem. 10 September 2018, https://doi.org/10.3389/fchem.2018.00401 (國外合作論文).

5.    Wen-Hua Chiou (邱文華)* and Po-Chou Chen (陳柏舟) “Synthesis of (±)-Aphanorphine Using Rh-Catalyzed Cyclohydrocarbonlyation" J. Org. Chem. 2017, 82, 8213-8219. https://dx.doi.org/10.1021/acs.joc.7b00923

6.    Keisuke Morisaki, Yusuke Sasano, Takahiro Koseki, Takuro Shibuta, Naoki Kanoh, Wen-Hua Chiou (邱文華), and Yoshiharu Iwabuchi* “Nazarov Cyclization Entry to Chiral Bicyclo[5.3.0]decanoid Building Blocks and Its Application to Formal Synthesis of (−)-Englerin A" Org. Lett. 2017, 19, 5142-5145. https://dx.doi.org/10.1021/acs.orglett.7b02428%20 (國外合作論文).

7.    Wen-Hua Chiou (邱文華)* and Hao-Yu Chen (陳皓俞) 　“Synthesis of Dendrobatid Alkaloid (+)-167B and (+)-209D and the Investigation on Diastereoselectivity using DFT Calculations" RSC Advances, 2017, 2 (2), 684-687. https://dx.doi.org/10.1039/c6ra24960d

8.    Wen-Hua Chiou (邱文華)*, Yu-Wei Wang (王裕崴), Chien-Lun Kao (高健倫), Po-Chou Chen (陳柏舟) and Chen-Chang Wu (吳承倉) “Rh-catalyzed Hydrocarbonylation of a Homoallylamine via N-H Activation and Application for Synthesis of Yohimbane Alkaloids " Organometallics 2014, 33 (16), 4240-4244. https://dx.doi.org/10.1021/om500498u

9.    Wen-Hua Chiou (邱文華)* and Yu-Min Chiang (江郁敏) “Synthesis of (−)-Epibatidine" RSC Advances 2014, 4 (22), 11444-11146. https://dx.doi.org/10.1039/c4ra00770k

10. Wen-Hua Chiou (邱文華),* Yu-Min Chiang (江郁敏) and Guei-Tang Chen (陳貴棠) “A Facile Synthesis of Enantiopure 7-Benzyloxycarbonyl-7-azabicyclo[2.2.1]heptane-2-carboxylic Acid" Tetrahedron: Asymmetry 2014, 25, 92-97. https://dx.doi.org/10.1016/j.tetasy.2013.11.010

11. Wen-Hua Chiou (邱文華),* Chien-Lun Kao (高健倫), Jui-Chi Tsai (蔡汭祁) and Yun-Man Chang (張耘嫚) “Domino Rh-catalyzed hydroformylation–double cyclization of o-amino cinnamyl derivatives: applications to the formal total syntheses of physostigmine and physovenine" Chem. Commun. 2013, 49, 8232-8234. https://dx.doi.org/10.1039/c3cc43257b

12. Wen-Hua Chiou (邱文華),* Guei-Tang Chen (陳貴棠), Chien-Lun Kao (高健倫) and Yu-Kai Gao (高煜凱), “Syntheses of (−)-pelletierine and (−)-homopipecolic acid" Org. Biomol. Chem. 2012, 10, 2518-2520. https://dx.doi.org/10.1039/c2ob06984a

13. Wen-Hua Chiou (邱文華),* Yi-Huei Lin (林益暉), Guei-Tang Chen (陳貴棠), Yu-Kai Gao (高煜凱), Yu-Che Tseng (曾于哲), Chien-Lun Kao (高健倫) and Jui-Chi Tsai 　(蔡汭祁) “Alkyne-Mediated Domino Hydroformylation/Double Cyclization: Mechanistic Insight and Synthesis of (±)-Tashiromine" Chem. Commun. 2011, 47, 3562-3564. https://dx.doi.org/10.1039/c0cc05646d

14. Wen-Hua Chiou (邱文華),* Yi-Huei Lin (林益暉) and Yu-Kai Gao (高煜凱) “Synthesis of (±)-Trans-indolizidine-8-carboxylic Acid" Synlett. 2011, 5, 663-664. https://dx.doi.org/10.1055/s-0030-1259558

15. Wen-Hua Chiou (邱文華),* Gau-Hong Lin (林高宏) 　and Chih-Wei Liang (梁智偉) “Facile Syntheses of Enantiopure 3-Hydroxypiperidine Derivatives and 3-Hydroxypipecolic Acids" J. Org. Chem. 2010, 75, 1748-1751. https://dx.doi.org/10.1021/jo902324h

16. Wen-Hua Chiou (邱文華),* Gau-Hong Lin (林高宏), Che-Cheng Hsu (許哲誠), Stephen J. Chaterpaul and Iwao Ojima “Efficient Syntheses of Crispine A and Harmicine by Rh-Catalyzed Cyclohydrocarbonylation." Org. Lett. 2009, 11, 2659-2662. https://dx.doi.org/10.1021/ol900702t

17. Wen-Hua Chiou (邱文華), Angèle Schoenfelder, André Mann and Iwao Ojima “Application of Rhodium-Catalyzed Cyclohydrocarbonylation to the Syntheses of Enantiopure Homokainoids" Pure Appl. Chem. 2008, 80, 1019-1024.

18. Wen-Hua Chiou (邱文華), Angèle Schoenfelder, Liang Sun, André Mann and Iwao Ojima* “Application of Rhodium-Catalyzed Cyclohydrocarbonylation to the Syntheses of Enantiopure Homokainoids" J. Org. Chem. 2007, 72, 9418-9425.

19. Wen-Hua Chiou (邱文華), Nobuhiro Mizutani and Iwao Ojima* "Recent Highly Efficient Synthesis of Azabicyclo[x.y.0]alkane Amino Acids and Congeners by Means of Rh-Catalyzed Cyclohydrocarbonylation " J. Org. Chem. 2007, 72, 1871-1882.

20. Wen-Hua Chiou (邱文華), Seung-Yub Lee and Iwao Ojima* "Recent advances in cyclohydrocarbonylation reactions" Can. J. Chem. 2005, 83, 681-692.

21. Nobuhiro Mizutani, Wen-Hua Chiou (邱文華) and Iwao Ojima* "New and efficient synthesis of azabicyclo[4.4.0]alkane amino acids by Rh-catalyzed cyclohydrocarbonylation." Org. Lett. 2002, (4), 4575-4578.


 

(B). Book Chapters:

1. “New Cyclization and Cycloaddition Reactions in Organic Synthesis”, Wen-Hua Chiou and Iwao Ojima, In New Methodologies and Techniques for a Sustainable Organic Chemistry, A. Mordini and F. Faigl (Eds.); NATO Science Series II: Mathematics, Physics and Chemistry, Vol. 246; Springer Science, Berlin (2008): pp 55-83.

2. “Amidocarbonylation, Cyclohydrocarbonylation and Related Reactions”, I. Ojima, C. Commandeur and W.-H. Chiou, In Comprehensive Organometallic Chemistry-III, Vol. 11, T. Hiyama and I. Ojima (Eds), Elsevier, Oxford, 2006; Chapter 11.15; pp 511-556.

 

(C). Oral Presentations since 2016:

1.    邱文華, "Recent Advances on Domino Hydroformylation Initiated- Cyclization Reactions and Synthetic Study on Kopsia alkaloid Kopsiyunnanine K"，108年5月17日，國內系所邀請演講，國立中央大學化學系，中壢市。

2.    Wen-Hua CHIOU (邱文華),“Arylalkyne mediated domino Hydroformylation /Double Cyclization: Diastereoselectivity Study and Application for the synthesis of 1-Azabicyclo[x.y.0]alkanes” Oral Presentation, the Pre-Meeting of the 13th International Symposium on Organic Reactions (Pre-ISOR-13), November 20-21, 2018, 台北市北投區。

3.    Kuei-Chen Chang (張桂禎), Wen-Wei Huang (黃文葦), and Wen-Hua CHIOU* (邱文華) “Synthetic Study on Allostemoamide by Rh-catalyzed Hydroformylation Double Cyclization” Poster Presentation, the 3rd Advanced Research Network on Cutting-Edge Organic Chemistry in Asia (ACP-4), November 1-5, 2018, Bangkok, Thailand.

4.    Zi-Ying Xiao (蕭資穎), Ke-Chiao Fu (傅柯喬), and Wen-Hua CHIOU* (邱文華) “Synthetic Study on Kopsia alkaloid Kopsiyunnanine K” Poster Presentation, the 3th Asian-European Symposium on Metal-Mediated Efficient Organic Synthesis (AES-2018), September 27-30, 2018, 新竹市。

5.    Wen-Hua CHIOU* (邱文華) “Syntheses of Chiral Piperidine Alkaloids from Tropinones” Oral Presentation, Bilateral-Symposium on Cutting-Edged Chemistry between Malaysia and Taiwan, January 15-16, 2018，新竹市。

6.    Wen-Hua CHIOU* (邱文華) and Po-Chou Chen (陳柏舟) “Synthesis of (±)-Aphanorphine using Rh-catalyzed Cyclohydrocarbonylation” Poster Presentation, the 3rd Advanced Research Network on Cutting-Edge Organic Chemistry in Asia (ACP-3), November 2-6, 2017, 西安市。

7.    Wen-Hua CHIOU* (邱文華), Invited Lectures by Asian Core Program Lectureship Award to Korea，"Recent Progress on Rh-catalyzed Hydroformylation Double Cyclization and Applications on Syntheses on Bioactive Alkaloids"。
(1).Department of Chemistry, Hankuk University of Foreign Studies (HUFS), May 11, 2017。
(2).Department of Chemistry, Korean Advanced Institute of Science and Technology (KAIST), May 12, 2017。
(3).Department of Chemistry, Seoul National University (SNU), May 15, 2017。

8.    邱文華, "Recent Advances on Domino Hydroformylation Initiated- Cyclization Reactions"，106年4月13日，國內系所邀請演講，中山醫科大學醫學應用化學系，台中市。

9.    邱文華, "Applications of Rh-catalyzed Domino Hydroformylation Double Cyclization for Syntheses of Alkaloids."，105年11月15日，國內系所邀請演講，國立彰化師範大學化學系，彰化市。

10. Wen-Hua CHIOU* (邱文華) and Kuo-Hsun Hsu (徐國訓) “Olefin-mediated Rh-catalyzed Domino Hydroformylation Double Cyclization: Applications on Syntheses of Indolizidine and Quinolizidine Alkaloids” Poster Presentation, the 2nd Advanced Research Network on Cutting-Edge Organic Chemistry in Asia (ACP-2), October 27-30, 2016, Daijeon, Korea.

 

 

國立中興大學化學系National Chung Hsing University Department of Chemistry

地址:台中市國光路250號 化學館 電話:04-22840411 傳真:04-22862547