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Charnsak Thongsornkleeb, Ph.D.

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Affiliation Laboratory of Organic Synthesis
Office R412, 4th Floor, Chemistry Research Building
Laboratory R619, 6th Floor, Chemistry Research Building
Telephone +662-553-8555 Ext. 8962 (Office), Ext. 8812 (Lab)
Fax +662-553-8545
E-mail charnsak@cri.or.th

Education

1996-2000B.Sc. (Chemistry, Minor Mathematics)University of Connecticut, Storrs, CT, USA
2000-2006Ph.D. (Organic Chemistry)Massachusetts Institute of Technology, Cambridge, MA, USA
2006-2008Postdoctoral TrainingCity University of New York, NY, USA

Research Interests

The current interest of our research lies in the development of new methodology for carbocyclic and heterocyclic intramolecular ring formations. We are currently investigating the employment of transition metal catalysts, particularly those of noble metals such as gold and platinum complexes, for these processes. Substrates which have been our investigative focus at present are alcohols and amines containing conjugated enyne moiety of various tether lengths. At the same time, we are also actively looking into the possibility of applying these catalytic systems in cascade or tandem reactions for the rapid construction of molecular architecture of high complexity. This will further aid the synthetic studies of a number of natural and unnatural compounds of interest and eventually lead to the total synthesis of these compounds.

Conjugated enyne moiety is a structural feature which have often been employed in synthetic applications due to their dense functionality which are suitable for many reactions. The alkyne portion embedded in these enynes can undergo nucleometallation with various nucleophiles upon activation with suitable catalysts.

Publications

  1. Supantanapong, N.; Chuangsoongnern, P.; Tummatorn, J.;* Thongsornkleeb, C.; Ruchirawat, S. One-pot sequential synthesis of 3-carbonyl-4-arylbenzo[f]indole and 3-carbonyl-4-arylnaphthofuran fluorophores. Org. Chem. Front. in press Full Text
  2. Akkachairin, B.; Tummatorn, J.;* Khamsuwan, N.; Thongsornkleeb, C.; Ruchirawat, S. Domino N2–Extrusion–Cyclization of Alkynylarylketone Derivatives for the Synthesis of Indoloquinolines and Carbocycle-Fused Quinolines. J. Org. Chem. 2018, 83, 11254-11268. Full Text
  3. Nimnual, P.; Norseeda, K.; Akkachairin, B.; Tummatorn, J.;* Laohapaisan, P.; Supantanapong, N.; Chuangsoongnern, P.; Thongsornkleeb, C.; Sittihan, S.; Ruchirawat, S.; Rodphon, W. Synthesis of β‐Naphthols and Naphthofuranones from ortho‐Alkynylarylketones via Sequential AgTFA‐Catalyzed Ketonization–Intramolecular Aldol Condensation: A Total Synthesis of Negundin A. Asian J. Org. Chem. 2018, 7, 932-945. Full Text
  4. Chaisan, N.; Kaewsri, K.; Thongsornkleeb, C.;* Tummatorn, J.; Ruchirawat, S. PtCl4-catalyzed cyclization of N-acetyl-2-alkynylanilines: A mild and efficient synthesis of N-acetyl-2-substituted indoles. Tetrahedron Lett. 2018, 59, 675–680. Full Text
  5. Kaewsri, W.; Norseeda, K.; Ruengsangtongkul, S.; Chaisan, N.; Thongsornkleeb, C.;* Tummatorn, J.; Ruchirawat, S. Synthesis of 2-Cyclohexenone-2-carboxylate and 4-Chloro-2-cyclohexenone-2-carboxylate Derivatives by Cyclization of Alkyne-Tethered 1,3-Ketoesters. Asian J. Org. Chem. 2018, 7, 203–211. Full Text
  6. Chuangsoongnern, P.; Surinrach, C.; Tummatorn, J.;* Thongsornkleeb, C.; Ruchirawat, S. Iodine-Mediated Cyclization of ortho-Alkynylaryl Ketones for the Synthesis of Indenone Derivatives. Eur. J. Org. Chem. 2017, 2017, 5102–5109. Full Text
  7. Akkachairin, B.; Tummatorn, J.;* Supantanapong, N.; Nimnual, P.; Thongsornkleeb, C.; Ruchirawat, S. Silver-Catalyzed Cyclization of ortho-Carbonylarylacetylenols for the Synthesis of Dihydronaphthofurans. J. Org. Chem. 2017, 82, 3727–3740. Full Text
  8. Jantaree, P.; Lirdprapamongkol, K.;* Kaewsri, W.; Thongsornkleeb, C.; Choowongkomon, K.; Atjanasuppat, K.; Ruchirawat, S.; Svasti, J. Homodimers of Vanillin and Apocynin Decrease the Metastatic Potential of Human Cancer Cells by Inhibiting the FAK/PI3K/Akt Signaling Pathway. J. Agric. Food Chem. 2017, 65, 2299–2306. Full Text
  9. Kaewsri, W.; Thongsornkleeb, C.;* Tummatorn, J.; Ruchirawat, S. Isomerizable (E/Z)-alkynyl-O-methyl oximes employing TMSCl–NCS in chlorinative cyclization for the direct synthesis of 4-chloroisoxazoles. RSC Adv. 2016, 6, 48666–48675. Full Text
  10. Norseeda, K.; Tummatorn, J.;* Krajangsri, S.; Thongsornkleeb, C.; Ruchirawat, S. Synthesis of 6-Alkyl-6 H-benzo[c]chromene Derivatives by Cyclization/Selective Ether Cleavage in One Pot: Total Synthesis of Cannabinol. Asian J. Org. Chem. 2016, 5, 792–800. Full Text
  11. Nimnual, P.; Tummatorn, J.;* Thongsornkleeb, C.; Ruchirawat, S. Utility of Nitrogen Extrusion of Azido Complexes for the Synthesis of Nitriles, Benzoxazoles and Benzisoxazoles. J. Org. Chem. 2015, 80, 8657–8667. Full Text
  12. Tummatorn, J.;* Poonsilp, P.; Nimnual, P.; Janprasit, J.; Thongsornkleeb, C.; Ruchirawat, S. Regioselective Synthesis of 3‑Bromoquinoline Derivatives and Diastereoselective Synthesis of Tetrahydroquinolines via Acid-Promoted Rearrangement of Arylmethyl Azides. J. Org. Chem. 2015, 80, 4516–4525. Full Text
  13. Aroonkit, P.; Thongsornkleeb, C.;* Tummatorn, J.;* Krajangsri, S.; Mungthin, M.; Ruchirawat, S. Synthesis of isocryptolepine analogues and their structure–activity relationship studies as antiplasmodial and antiproliferative agents. Eur. J. Med. Med. 2015, 94, 56–62. Full Text
  14. Tummatorn, J.;* Thongsornkleeb, C.; Ruchirawat, S.; Thongaram, P.; Kaewmee, B. Convenient and Direct Azidation of sec-Benzyl Alcohols by Trimethylsilyl Azide with Bismuth(III) Triflate Catalyst. Synthesis 2015, 47, 323–329. Full Text
  15. Tummatorn, J.;* Krajangsri, S.; Norseeda, K.; Thongsornkleeb, C.; Ruchirawat, S. A new synthetic approach to 6-unsubstituted phenanthridine and phenanthridine-like compounds under mild and metal-free conditions. Org. Biomol. Chem. 2014, 12, 5077–5081. Full Text
  16. Maibunkaew, T.; Thongsornkleeb, C.;* Tummatorn, J.; Bunrit, A.; Ruchirawat, S. Practical and Metal-Free Electrophilic Aromatic Halogenation by Interhalogen Compounds Generated in situ from N-Halosuccinimide and Catalytic TMSCl. Synlett 2014, 25, 1769–1775. Full Text
  17. Tummatorn, J.;* Gleeson, M. P.; Krajangsri, S.; Thongsornkleeb, C.; Ruchirawat, S. ZrCl4-promoted facile synthesis of indole derivatives. RSC Adv. 2014, 4, 20048–20052. Full Text
  18. Tummatorn, J.;* Thongsornkleeb, C.; Ruchirawat, S.; Gettongsong, T. Synthesis of 2,4-unsubstituted quinoline-3-carboxylic acid ethyl esters from arylmethyl azides via a domino process. Org. Biomol. Chem. 2013, 11, 1463–1467. Full Text
  19. Thongsornkleeb, C.;* Rabten, W.; Bunrit, A.; Tummatorn, J.; Ruchirawat, S. Facile access to 2,5-disubstituted-4-chloromethyl-3-iodofuran derivatives via ICl-mediated cyclization of 1-alkyl-2-alkynylallylic alcohols. Tetrahedron Lett. 2012, 53, 6615–6619. Full Text
  20. Tummatorn, J.;* Thongsornkleeb, C.; Ruchirawat, S. Acid-promoted rearrangement of arylmethyl azides: applications toward the synthesis of N-arylmethyl arenes and polycyclic heteroaromatic compounds. Tetrahedron 2012, 68, 4732–4739. Full Text
  21. Bunrit, A.; Ruchirawat, S.; Thongsornkleeb, C.* A simple microwave-assisted preparation of 2-bromo-1-alkenes from 1-alkynes using the LiBr–TMSCl–TEAB reagent system. Tetrahedron Lett. 2011, 52, 3124–3127. Full Text
  22. Fearnley, S. P.;* Thongsornkleeb, C. Oxazolone Cycloadducts as Heterocyclic Scaffolds for Alkaloid Construction: Synthesis of (±)-2-epi-Pumiliotoxin C. J. Org. Chem. 2010, 75, 933–936. Full Text
  23. Thongsornkleeb, C.; Danheiser, R. L.* A Practical Method for the Synthesis of 2-Alkynylpropenals. J. Org. Chem. 2005, 70, 2364–2367. Full Text
  24. Bailey, W. F.;* England, M. D.; Mealy, M. J.; Thongsornkleeb, C.; Teng, L. Facile O-Deallylation of Allyl Ethers via SN2' Reaction with tert-Butyllithium. Org. Lett. 2000, 2, 489–491. Full Text

Presentations

Oral Presentations

  1. Ruengsangtongkul, S.; Chaisan, N.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. “Pd(II)/CAN-promoted intramolecular oxidative cyclization of -propargylated 1,3-ketoesters to 2,4-diacylfurans” Presented at The 13th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-13), Bangkok, Thailand, November 1–4, 2018.
  2. Ruengsangtongkul, S.; Chaisan, N.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. “Pd(II)-Ce(IV) cooperative induction of intramolecular oxidative cyclization of α-propargylated 1,3-ketoesters: A rapid construction of 2,4-diacylfurans” Presented at the 256th American Chemical Society National Meeting, Boston, MA, USA, August 19–23, 2018.
  3. Thongsornkleeb, C. “Efficient and Practical Halogenation Reactions of Organic Compounds” Presented at Chiba University, Chiba, Japan, September 2, 2016.
  4. Thongsornkleeb, C. “Halogenation Reactions for Improving Bioactivities of Medicinal Compounds” Presented at The 3rd Symposium of SPU Innovative Project for Pharmaceutical Analyses of Covalent Modification in Biomolecules, Showa Pharmaceutical University, Machida, Japan, August 31–September 1, 2016.
  5. Thongsornkleeb, C.; Kaewsri, W.; Tummatorn, J.; Ruchirawat, S. “Efficient, Practical and Metal-Free Halogenation of Organic Compounds” Presented at The 4th Junior International Conference on Cutting-Edge Organic Chemistry in Asia (JICCEOCA-4), Bangkok, Thailand, November 29–30, 2014.
  6. Thongsornkleeb, C.; Maibunkaew, T.; Bunrit, A.; Tummatorn, J.; Ruchirawat, S. “Hydrohalogenation and Halogenation by in situ Generation of Reactive Halogenating Species & Isocryptolepine Analogues Synthesis and Bioactivities Evaluation” Presented as a part of Asian CORE Program (ACP) Lectureship Tour, Taiwan, March 2–8, 2014.
  7. Thongsornkleeb, C.; Fearnley, S. P. “Intramolecular Diels-Alder Reactions of Oxazolone: Approaches Toward Total Synthesis of Pumiliotoxin C and Related Alkaloids” Presented at the 234th American Chemical Society National Meeting, Boston, MA, USA, August 19-23, 2007.

Poster Presentations

  1. Norseeda, K.; Chaisan, N.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. “Convenient Access to 4-Chloroisocoumarins via TMSCl-Catalyzed Chlorinative Cyclization of o-Alkynylaryloate Esters with NCS” Presented at The 12th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-12) The 3rd Advanced Research Network on Cutting-Edge Organic Chemistry in Asia (ARNCEOCA-3), Xi'an, China, November 1–5, 2017.
  2. Thongsornkleeb, C.; Kaewsri, W.; Tummatorn, J.; Ruchirawat, S. “TfOH-Promoted Cyclization of δ-Alkynyl-β-Ketoesters for the Synthesis of Functionalized Cyclohexenones” Presented at The 11th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-11) The 2nd Advanced Research Network on Cutting-Edge Organic Chemistry in Asia (ARNCEOCA-2), Daejeon, Korea, October 27–30, 2016.
  3. Aroonkit, P.; Thongsornkleeb, C.; Tummatorn, J.; Krajangsri, S.; Mungthin, M.; Ruchirawat, S. “Halogenation of Isocryptolepine: Structure-Activity Relationship Studies in Antiplasmodial and Antiproliferative Properties” Presented at The 10th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-10) The 6th New Phase International Conference on Cutting-Edge Organic Chemistry in Asia (NICCEOCA-6), Kaohsiung, Taiwan, November 2–6, 2015.
  4. Thongsornkleeb, C.; Kaewsri, W.; Tummatorn, J.; Ruchirawat, S. “A Practical Synthesis of Haloisoxazoles via Electrophilic Halocyclization” Presented at The 9th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-9) The 5th New Phase International Conference on Cutting-Edge Organic Chemistry in Asia (NICCEOCA-5), Petaling Jaya, Malaysia, December 2–4, 2014.
  5. Thongsornkleeb, C.; Maibunkaew, T.; Bunrit, A.; Tummatorn, J.; Ruchirawat, S. “Practical and Metal-Free Electrophilic Aromatic Halogenation with N-halosuccinimide in the Presence of Catalytic Chlorotrimethylsilane” Presented at The 8th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-8) The 4th New Phase International Conference on Cutting-Edge Organic Chemistry in Asia (NICCEOCA-4), Osaka, Japan, November 25–28, 2013.
  6. Thongsornkleeb, C.; Rabten, W.; Bunrit, A.; Tummatorn, J.; Ruchirawat, S. “Facile Access to 2,5-Disubstituted-4-Chloromethyl-3-Iodofuran Derivatives via ICl-Mediated Cyclization of 1-Alkyl-2-alkynylallylic Alcohols” Presented at The 7th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-7) The 3rd New Phase International Conference on Cutting-Edge Organic Chemistry in Asia (NICCEOCA-3), Nanyang Technological University, Singapore, December 11–14, 2012.
  7. Thongsornkleeb, C.; Rabten, W.; Bunrit, A.; Tummatorn, J.; Ruchirawat, S. “Facile Access to 2,5-Disubstituted-4-Chloromethyl-3-Iodofuran Derivatives via ICl-Mediated Cyclization of 1-Alkyl-2-alkynylallylic Alcohols” Presented at the 12th Annual Thailand’s Research Fund Meeting, Cha-Am, Petchburi, Thailand, October, 2012.

Students Supervised

Current Thesis Advisees

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Mr. Krissada Norseeda
Ph.D. student (2014-Present)

Ms. Nattawadee Chaisan
Ph.D. student (2016-Present)

Ms. Kunlayanee Punjajom
M.Sc. student (2017-Present)

Current Thesis Co-Advisees


Mr. Phongprapan Nimnual
Ph.D. student (2014-Present)

Current Research Assistant


Ms. Sureeporn Ruengsangtongkul
Research Assistant (2015-Present)

Former Thesis Advisees : Ph.D. Students


Dr. Wilailak Kaewsri
Ph.D. student (2013-2018)

Former Thesis Advisees : Master Students

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Dr. Anon Bunrit
M.Sc. student (2008-2010)
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Dr. Wangchuk Rabten
M.Sc. student (2010-2012)
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Ms. Tapanee Maibunkaew
M.Sc. student (2012-2014)
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Mr. Pasuk Aroonkit
M.Sc. student (2012-2014)
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Mr. Piyapratch Poonsilp
M.Sc. student (2012-2014)

Group Activities and Announcements

Pizza Time! : July 2015

Stang's Last Day in the Lab : December 18, 2015

Congratulations to Dr. Wilailak Kaewsri on completing her Ph.D. on June 11, 2018 !!!

Great Organic Chemistry Resources on the Internet