Dr. P. Chiu¡@¡@¡@»¯Ä_¶M³Õ¤h



B.Sc. (Hons), M.Sc., Ph.D. University of Toronto
Postdoctorate: Columbia University

Editorial Board Member:
Organic and Biomolecular Chemistry (Royal Society of Chemistry)
Journal of Heterocyclic Chemistry (Wiley)

    
   
                       
Office:

Room 604
Chong Yuet Ming Chemistry Building
The University of Hong Kong
Pokfulam Road
Hong Kong

        
Tel. No.:

E-Mail:
 (852) 2859 8949

pchiu@hku.hk   		 
 
  Research Interests
Selected Publications
Awards
Pictures of Our Group

Detailed CV 		 
   
             
Research Interests            
             
 

Development of new organic synthetic methodology, asymmetric synthesis, total synthesis of natural products, bioactivity-directed isolation of natural products from Chinese medicinal herbs, and studies on their chemical biology and therapeutic applications, medicinal chemistry.

Total Synthesis of Natural Products

We have an ongoing program in the synthesis of architecturally and biologically interesting compounds. Our completed targets include the antifungal and anti-tumor pseudolaric acids which have been isolated from a Chinese medicinal herb tujinpi (Pseudolarix amabilis); indicol, an antifeedant isolated from Dictyota indica, lucinone from the antispasmodic medicinal plant Jasonia glutinosa. Our current targets include the anti-bacterial guanacastepene A from a fungus of Daphnopsis americana, curcumol from ezhu, the rhizomes of the Chinese medicinal plant Curcuma wenyujin, which has been used to treat cervical cancer, cortistatin A, a picomolar anti-angiogenic agent; dolatriol, a cytotoxic natural product isolated from Dolabella auricularia.


Novel Reactions Mediated by Copper Hydrides

  1. Reductive aldol reaction: We have developed a general method for the synthesis of authentic copper enolates in the absence of other metal counterions using [(Ph3P)CuH]6 and we have successfully carried out synthetic reactions using these reactive intermediates. We have carried out reductive intramolecular aldol reactions, both stoichiometrically and catalytically in copper hydride, which afford cyclized products with good yields and diastereoselectivities.


  2. Copper hydride-mediated hydrostannation: We have discovered that
    [(Ph3P)CuH]6, or copper hydride generated in situ from CuCl, KOtBu, Ph3P and stannane are effective in mediating the hydrostannation of alkynones and alkynoates with higher selectivity for α-stannation than typical palladium catalysts.


Studies on the cascade reactions of ylides from intramolecular carbene cyclizations

Ylide intermediates can be generated from the intramolecular reactions of carbenes and heteroatomic functional groups, such as carbonyl groups and ethers. These reactive intermediates can in turn undergo tandem reactions which stereoselectively afford products with a tremendous escalation of complexity. We are studying these reactions to exploit them for the synthesis of natural products.

Synthesis of oxabicyclic compounds and their use in organic synthesis

Because the reactions of oxabicyclic compounds are generally highly stereoselective, oxabicyclic substrates are valuable intermediates that can be exploited for the synthesis of complex targets. Our efforts in this area are to develop novel methods to synthesize oxabicyclic compounds, as well as to design novel methods to induce their ring opening. We have optimized and developed a [4+3] cycloaddition reaction using epoxy enol silanes as the three carbon electrophile, resulting in highly functionalized polycyclic structures in good to excellent yields.


  		 
 
[ Top ]
  Selected Publications            
                 
   

  1. A Rhodium Carbene Cyclization-Cycloaddition Cascade Strategy toward the Pseudolaric Acids. Chiu, P.*; Chen, B.; Cheng, K. F. Org. Lett. 2001, 3, 1721-1724.

  2. Tandem Conjugate Reduction-Aldol Cyclizations Using Stryker's Reagent. Chiu, P.; Szeto, C. P.*; Geng, Z.; Cheng, K. F. Org. Lett. 2001, 3, 1901-1903.

  3. An Expedient Preparation of Stryker's Reagent. Chiu, P. *; Li, Z.; Fung, K. C. M. Tetrahedron Lett. 2003, 44, 455-457.

  4. A Tandem Metal Carbene Cyclization-Cycloaddition Approach to the Pseudolaric Acids. Chen, B.; Ko, R. Y. Y.; Yuen, M. S. M; Cheng, K. F.; Chiu, P.* J. Org. Chem. 2003, 68, 4195-4205.

  5. Desymmetrizations of Meso Oxabicyclic Compounds by Asymmetric C-H Insertion. Chiu, P.*; Zhang, X.; Ko, R. Y. Y. Tetrahedron Lett. 2004, 45, 1531-1534.

  6. An Expeditious Nazarov Cyclization Strategy to the Hydroazulene Core of Guanacastepene A. Chiu, P.*; Li, S. Org. Lett. 2004, 6, 613-616.

  7. A Synthesis of the Tetracyclic Carboskeleton of Isaindigotidione. Poon, C. Y.; Chiu, P.* Tetrahedron Lett. 2004, 45, 2985-2988.

  8. New Triterpene Peroxides from Pseudolarix kaempferi. Zhou, T.; Zhang, H.; Zhu, N.; Chiu, P.* Tetrahedron 2004, 60, 4931-4936.

  9. Reductive and Catalytic Reductive Aldol Cyclizations of Alkynediones Induced by Stryker¡¦s Reagent. Chiu, P. *; Leung, S. K. Chem. Commun. 2004, 2308-2309.

  10. Organosilanes in Copper-mediated Conjugate Reductions and Reductive Aldol Reactions, Chiu, P. Synthesis 2004, 2210-2215.

  11. Reductive Intramolecular Henry Reactions Induced by Stryker¡¦s Reagent. Chiu, P.*; Chung, W. K. Synlett 2005, 55-58.

  12. Dihydrochalcones from the Leaves of PIERIS JAPONICA. Yao, G.-M.; Ding, Y.; Quo, J.-P.; Wang, H.-B.; Wang, Y.-B.; Ding, B.-Y.; Chiu, P.; Qin, G.-W.* J. Nat. Prod. 2005, 68, 392-396.

  13. Metal-catalyzed cyclopropanations on the 8-oxabicyclo[3.2.1]octene template. Leung, S. K.; Chiu, P.* Tetrahedron Lett. 2005, 46, 2709.

  14. Application of the Carbene Cyclization Cycloaddition Cascade in Total Synthesis. Chiu, P. Pure and Appl. Chem. 2005, 77, 1183-1189.

  15. Pseudolaric acid B, a novel class of microtubule-destabilizing agent circumvents a multi-drug resistant phenotype and exhibits antitumor activity in vivo. Wong, V. K. M.; Chiu, P.; Chung, S. S. M.; Chow, L. M. C.; Zhao, Y. Z.; Yang, B. B.; Ko, B. C. B.* Clin. Cancer Res. 2005, 11 (16), 6002-6011.

  16. Copper-catalyzed hydrostannation of activated alkynes. Leung, L. T.; Leung, S. K.; Chiu, P.* Org. Lett. 2005, 7, 5249-5252.

  17. Allenes as dipolarophiles in the intramolecular carbene cyclization cycloaddition cascade reaction. Zhang, X.; Ko, R. Y. Y.; Li, S.; Miao, R.; Chiu, P.* Synlett 2006, 1197-1200.

  18. Total synthesis of pseudolaric acid A. Geng, Z.; Chen, B.; Chiu, P.* Angew. Chem. Int. Ed. 2006, 26, 6197-6201.

  19. The application of non-cross-linked polystyrene-supported triphenylarsine in Stille coupling reactions. Lau, K. C. Y.; Chiu, P.* Tetrahedron Lett. 2007, 48, 1813-1816.

  20. Regioselective hydrostannation of activated alkynes catalyzed by copper. Miao, R.; Li, S.; Chiu, P.* Tetrahedron 2007, 63, 6737-6740.

  21. Total Synthesis of (-)-Indicol. Lam, S. K.; Chiu, P.* Chem.-Eur. J. 2007, 13, 9589-9599.

  22. Acid-promoted sequential cationic cyclizations for the synthesis of (¡Ó)-taiwaniaquinol B. Li, S.; Chiu, P.* Tetrahedron Lett. 2008, 49, 1741-1744.

  23. Inter- and intramolecular [4+3] cycloadditions using epoxy enol silanes as functionalized oxyallyl cation precursors. Chung, W. K.; Lam, S. K.; Lo, B.; Liu, L. L.; Wong, W.-T., Chiu, P.* J. Am. Chem. Soc. 2009, 131, 4556-4557.

    This publication was highlighted in Organic Chemistry Highlights:
    http://www.organic-chemistry.org/Highlights/2009/28December.shtm

  24. The Rhodium-Catalyzed Carbene Cyclization Cycloaddition Cascade Reaction of Vinylsulfonates. Shi, B.; Merten, S., Wong, D. K. Y.; Chu, J. C. K.; Liu, L. L.; Lam, S. K.; Jager, A.; Wong, W.-T.; Chiu, P.*; Metz, P.* Adv. Synth. Catal. 2009, 351, 3128-3132.

  25. Ene Reactions. Lam, S. K.; Chiu, P. In: Science of Synthesis; de Meijere, A. Ed.; Thieme: Stuttgart, 2009; Vol. 47, p. 737-754.

  26. Alisol B, a novel inhibitor of the SERCA pump, induces autophagy, ER-stress and apoptosis. Law, B. Y. K.; Wang, M.; Ma, D.-L.; Al-Mousa, F.; Michelangeli, F.; Wong, A.; ;Ng, M.; -To, K.-F.; Mok, A. Y. F.; Ko, R. Y. Y.; Lam, S. K.; Chen, F.; Che, C.-M.; Chiu, P.*; Ko, B. C. B.* Mol. Cancer Ther. 2010, 69, 718-730.

  
   
[ Top ]
                 
Awards
                 

2003 Summer Symposium of Synthetic Organic Chemistry Lectureship Awardee

2006 The 1st International Conference on Cutting-edge Organic Chemistry in Asia CORE Program Lectureship Award Sponsored by Korean Science and Engineering Foundation (KOSEF-CMDS/CBMH)

2006 The 1st International Conference on Cutting-edge Organic Chemistry in Asia CORE Program Lectureship Award Sponsored by Nanyang Technological University, Singapore

2007 The 2nd International Conference on Cutting-edge Organic Chemistry in Asia, Asian CORE Program Lectureship Award, Sponsored by the National Science Foundation of China (NSFC)

2007 The 2nd International Conference on Cutting-edge Organic Chemistry in Asia, Asian CORE Program Lectureship Award, Sponsored by the Japan Society for Promotion of Sciences (JSPS)

The 2007 University Research Output Prize for the Faculty of Science, Awarded by the University Research Committee, The University of Hong Kong

Postdoctoral Scholarships and Awards

  • 1994-1995 National Science & Engineering Research Council of Canada Postdoctoral Fellowship

 

  
[ Top ]
 
Pictures of Our Group
   
 

Group Reunion at Parklane Hotel Café, July 2007

 

Students and demonstrators of the CHEM3403 course "Integrated Organic Synthesis" visited the Lonza Research and Development Center in Nansha, Guangzhou on March 16, 2009.


   
 
Former group members

Name Position Year Present Position
Rex Szeto
(B. Sc. HKU)		 M. Phil. 1997-2000 Form 7 teacher,
Po Leung Kuk Choi Kai Yau School
Bin Chen
(B. Sc. Shanghai Medical U./Fudan U.)		 Ph. D. 1997-2001 Research Scientist, Lundbeck Research U.S.A., Paramus N.J.
Rebecca Yuen Yi Ko
(B. Sc. HKU)		 Ph. D. 1999-2003 Lecturer in Chemistry, HKU SPACE
Skarlett Sze Kar Leung
(B. Sc. HKU)		 Ph. D. 1999-2004 Assistant Supervisor, Intertek HK Ltd.
Zhengning Li
(Ph. D., Dalian Institute of Chem. Phys.)		 Postdoctoral research associate 2000-2001;
2003-2004		 Professor, Dept of Chemistry,
Dalian U.
Dianna Ch Yan Poon
(B. Sc. HKU)		 Ph. D. 2000-2004 Laboratory Executive, SGS Hong Kong Ltd.
Zhe Geng
(M. Sc. Beijing Normal U.)		 Ph. D. 2000-2004 Synthetic chemist, Toronto Research Chemicals
Xiaomei Zhang
(Ph. D., Chengdu Institute of Org. Chem.) 		Postdoctoral research associate 2001-2002 Professor, Chengdu Institute of Organic Chemistry
Wing Ki Chung
(B. Sc. HKU)		 Ph. D. 2001-2006 Laboratory Analyst, Springborn Testing Labs HK Ltd.
Kelvin Chi Ming Fung
(B. Sc. HKU)		 Ph. D. 2001-2006 Research scientist, Lonza Group Ltd. Switzerland
Secant Sze Kui Lam
(B. Sc. HKU)		 Ph. D. 2001-2006 PDF, The University of Hong Kong
Yunhong Zheng
(Ph. D., Shanghai Medical U.)		 Postdoctoral research associate 2002-2003 Assistant Professor, Shanghai Institute of Materia Medica
Shuoliang Li
(B. Sc., M. Phil Lanzhou U)		 Ph. D. 2002-2006 Principal Scientist, Suzhou Novartis Pharma Technology Co., Ltd.
Vincent Kam Wai Wong
(B. Sc. HKUST)		 Ph. D.
(Co-supervised with Dr. B.C.B. Ko)		 2002-2006 PDF, School of Chinese Medicine, HKBU
Tianxi Zhou
(B. Sc., Shanghai Yeyu Pharmaceutical College)		 Research associate 2003 Research associate, Shanghai Institute of Materia Medica
Xingxian Zhang
(Ph. D., Lanzhou U.) 		Postdoctoral research associate 2003-2004 Assistant Professor, College of Pharmaceutical Science, Zhejiang U. of Technology
Kelvin Chi Yin Lau
(B. Sc. HKU) 		Ph. D. 2003-2007 Lecturer in Chemistry, Beacon College
Bonnie Lai To Leung
(B. Sc. HKU)		 Ph. D. 2004-2008 PDF, The University of Hong Kong
Ru Miao
(Ph. D., ICCAS, Beijing)		 Postdoctoral research associate 2005-2006 PDF, National U. of Singapore
Betty Yuen Kwan Law
(B. Sc. HKUST)		 Ph. D.
(Co-supervised with Dr. B.C.B. Ko)		 2005-2009 Research Associate, The University of Hong Kong
Gunnar Ehrlich
(Ph. D. U of Hannover)		 DFG Postdoctoral fellow 2007-2008 Dept of Chemical Safety, Umwelt Bundes Amt, Germany




Present group members

Name Position Years
Dr. Secant Lam Postdoctoral Fellow 2006-
Dr. Bonnie Leung Postdoctoral Fellow 2009-
Dr. Guo Wei Postdoctoral Fellow 2009-
Dr. Betty Law Research Associate 2009-
Lok Lok Liu Ph. D. Candidate 2006-
Brian Tsz Kiu Lo Ph. D. Candidate 2006-
Ally Ninglin Li M. Phil. candidate 2007-
Emily Shuk Mei Lam Ph. D. Candidate 2008-
Johnny Kong Ching Wong Ph. D. Candidate 2008-
Sarah Lam Ph. D. Candidate 2009-
Baojian Li Ph. D. candidate 2009-
Liping Kuang Ph. D. Candidate 2010-
Jack Jun Ou Ph. D. Candidate 2010-
 
   
[ Top ]