Staff – Medicinal Chemistry

Assoc. Prof. Dr. Jumreang Tummatorn

Category Staff - Medicinal Chemistry
26 Jan 2023
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Name : Assoc. Prof. Dr. Jumreang Tummatorn (Research Scientist II)
Office Address : Room : R619
Laboratory of Medicinal Chemistry
54 Kamphaeng Phet 6 Talat Bang Khen, Lak Si, Bangkok 10210, Thailand
Tel : +66 2553 8555 (ext. 3089)
Email : [email protected]

Research Interests
Synthetic methodology
Asymmetric catalysis
Total synthesis of natural products

Education
2004-2008 Ph.D Organic Chemistry, Chulalongkorn University, Bangkok, Thailand
2002-2004 M.Sc. Organic Chemistry, Chulalongkorn University, Bangkok, Thailand
1998-2002 B.A. Chemistry, Burapha University, Chonburi, Thailand

Work Experiences
2007-2008 Research assistant, Chulabhorn Research Institute, Thailand
2009 International Bio Service
2009-2011 Postdoctoral Fellow, Florida State University
2009-2012 Lecturer in chemical biology program Chulabhorn Graduate Institute
2011-2015 Research Scientist Chulabhorn Research Institute
2014-2018 Lecturer in chemical biology program Chulabhorn Graduate Institute
2018-present Research Scientist II Chulabhorn Research Institute
2019-present Associate Professor Chulabhorn Graduate Institute

Awards
2006-2008 “The Royal Golden Jubilee Scholarship from Thailand Research Fund
for Ph.D. scholarship program, 2006-2008”
2009 รางวัลการศึกษายอดเยี่ยมขั้นวิทยาศาสตรดุษฏีบัณฑิต จากมูลนิธิศาสตราจารย์ ดร.แถบ นีละนิธิ 2009
2014 Best Poster Award from the 14th Annual Conference of the Thailand Research Fund (TRF)
2016 Asian CORE Program (ACP) Lectureship Award to Taiwan, presented at the 11th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-11), Taiwan (26-31 October 2016)
2016 Asian CORE Program (ACP) Lectureship Award to Korea, presented at the 11th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-11), Korea (26-31 October 2016)
2019 Asian CORE Program (ACP) Lectureship Award to Hong Kong, presented at the 14th International Conference on Cutting-Edge Organic Chemistry in Asia (ICCEOCA-14), Japan (26-29 September 2019)
2019 L’Oréal-UNESCO For Women in Science Fellowships 2019 (Physical Sciences), October 4th 2019

Publications
Selected Publications

  1. Jaithum, K.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. Synergistic Lewis–Brønsted Acid Catalysis in Cascade Cyclization of ortho-Alkynylaryl Cyclopropylketones for the Synthesis of 2, 3-Dihydronaphtho [1, 2-b] furans. J. Org, Chem.  2022(Accepted Manuscripts) (Selected as an issue’s front cover)
  2. Rodphon, W.; Jaithum, K.; Linkhum, S.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. Synthesis of Naphtho [2, 3-d] oxazoles via Ag (I) Acid-Mediated Oxazole-Benzannulation of ortho-Alkynylamidoarylketones. J. Org, Chem.  2022. (Accepted Manuscripts) (Selected as an issue’s front cover)
  3. Khorphueng, P.; Tummatorn, J.; Patumanon, W.; Thongsornkleeb, C.; Chonradeenitchakul, S.; Ruchirawat, S. Photoinduced C–C bond cleavage for the synthesis of 2, 4-disubstituted-1-naphthols from indenone derivatives and sulfoxonium ylide. Org. Biomol. Chem.  2022, 20, 5520-5524. (Selected as an issue’s front cover)
  4. Chaisan, N.; Ruengsangtongkul, S.; Thongsornkleeb, C.;* Tummatorn, J.; Ruchirawat, S. Dihalooxygenation of Alkynes and Alkynols: Preparation of 2,2-Dihaloketones and gem-Dihalolactols. Synlett 2022. (Accepted Manuscripts)
  5. Ruengsangtongkul, S.; Kuribara, T.; Chaisan, N.; Tummatorn, J.; Thongsornkleeb,C.;* Ruchirawat, S. Ceric Ammonium Nitrate‐Promoted Oxidative Coupling of Terminal Alkynes and 1,3‐Ketoesters: A Synthesis of Unsymmetrical 1,1,2‐Triacylalkenes. Synlett 2022 (Accepted Manuscripts)
  6. Thongsornkleeb, C.; Tummatorn, J.;* Ruchirawat, S. A Compilation of Synthetic Strategies to Access the Most Utilized Indoloquinoline Motifs. Chem. Asian J. 2022, 7, e202200040 (Selected as an issue’s front cover)
  7.  Laohapaisan, P.; Lumyong, K.; Tummatorn, J.;* Thongsornkleeb, C.; Chatwichien, J.; Supantanapong, N.; Ruchirawat, S. Ag(I)-Catalyzed/Acid-Mediated Cascade Cyclization of ortho-Alkynylaryl-1,3-dicarbonyls to Access Arylnaphthalenelactones and Furanonaphthol Libraries via Aryl-Disengagement. Chem. Asian J. 2021, 7, e202101212. (Selected as an issue’s cover)
  8. Rodphon, W.; Laohapaisan, P.; Supantanapong, N.; Reamtong, O.; Ngiwsara, L.; Lirdprapamongkol, K.;* Thongsornkleeb, C.; Khunnawutmanotham, N.; Tummatorn, J.;* Svasti, J.; Ruchirawat, S. Synthesis of Isocryptolepine-Triazole Adducts and Evaluation of Their Cytotoxic Activity. ChemMedChem 2021, 16, 3750-3762.
  9. Reamtong, O.; Lapmanee, S.; Tummatorn, J.;* Palavong, N.; Thongsornkleeb, C.; Ruchirawat, S. Synthesis of Benzoazepine Derivatives via Azide Rearrangement and Evaluation of Their Antianxiety Activities. ACS Med. Chem. Lett. 2021, 12, 1449–1458. (Selected as an issue’s cover).
    10. Jaithum, K.; Tummatorn, J.;* Boekfa, B.; Thongsornkleeb, C.; Chainok, K.; Ruchirawat, S.
  10. Jaithum, K.; Tummatorn, J.;* Boekfa, B.; Thongsornkleeb, C.; Chainok, K.; Ruchirawat, S. Diastereoselective Synthesis of Spirocyclic Ether from ortho-Carbonylarylacetylenols via Silver-Catalyzed Cyclization under Acidic Conditions. Adv. Synth. Catal. 2021, 363, 3812-3834.
  11. Thongsornkleeb, C.; Tummatorn, J.;* Ruchirawat, S. Utilization of ortho-alkynylarylcarbonyl derivatives for creating structurally diverse chemical compounds (Review), Org. Biomol. Chem. 2021, Org. Biomol. Chem. 2021,19, 5982-5998.
  12. Chaisan, N.; Ruengsangtongkul, S.; Tummatorn, J.; Ruchirawat, S.; Chainok, K.; Thongsornkleeb, C.;* Dibrominative Spirocyclization of 2‑Butynolyl Anilides: Synthesis of 2 gem-Dibromospirocyclic Benzo[d][1,3]oxazines and Their 3 Application in the Synthesis of 4H‑Furo[3,2‑b]indoles. J. Org. Chem. 2021, 86, 4671–4698.
  13. Punjajom, K.; Tummatorn, J.; Thongsornkleeb, C.;* Ruchirawat, S.  PdCl2‐Catalyzed Oxidative Cyclization of N‐(2’‐Alkynylaryl)‐1,3‐ketoamides: Synthesis of 3,4‐Diacyl‐2‐quinolones, Asian J. Org. Chem. 2021, 10, 906-917.
  14. Rodphon, W.; Thongsornkleeb, C.; Tummatorn, J.;* Ruchirawat, S. Synthesis of 4‐Acylchromene via Highly Chemoselective Iodine‐Catalyzed Cyclization of Alkynylarylether Dimethylacetals. Chem. Asian J. 2020, 15, 3475–3486.
  15.  Akkachairin, B.; Rodphon, W.; Reamtong, O.; Mungthin, M.; Tummatorn, J.;* Thongsornkleeb, C.; Ruchirawat, S. Synthesis of neocryptolepines and carbocycle-fused quinolines and evaluation of their anticancer and antiplasmodial activities. Bioorg. Chem. 2020, 98, 103732.
  16. Norseeda, K.; Chaisan, N.; Thongsornkleeb, C.;* Tummatorn, J.; Ruchirawat, S. Metal-Free Synthesis of 4-Chloroisocoumarins by TMSCl-Catalyzed NCS-Induced Chlorinative Annulation of 2-Alkynylaryloate Esters. J. Org. Chem. 2019, 84, 16222-16236
  17. Laohapaisan, P.; Chuangsoongnern, P.; Tmmatorn, J.; * Thongsornkleeb, C.; Ruchirawat, S. Divergent Synthesis of 3-Hydroxyfluorene and 4-Azafluorene Derivatives from ortho-Alkynylarylketones. J. Org. Chem. 2019, 84, 14451-14460. (Selected as an issue’s cover).
  18. Rujimongkon, K.; Mungthin, M; Tummatorn, J.; Ampawong, S.; Adisakwattana, P.; Boonyuen, U.; Reamtong, O.* Proteomic analysis of Plasmodium falciparum response to isocryptolepine derivative. PLOS ONE2019, 14(8): e0220871.
  19. Tummatorn, J.;* Punjajom, K.; Rodphon, W.; Ruengsangtongkul, S.; Chaisan, N.; Lumyong, K.; Thongsornkleeb, C.; Nimnual, P.; Ruchirawat, S. Chemoselective Synthesis of 1,1-Disubstituted Vinyl Triflates from Terminal Alkynes Using TfOH in the Presence of TMSN3. Org. Lett. 2019, 21, 4694-4697.
  20. Nimnual, P.; Tummatorn, J.;* Boekfa, B.; Thongsornkleeb, C.; Ruchirawat, S.; Piyachat, P.; Punjajom, K. Construction of 5-Aminotetrazoles via in Situ Generation of Carbodiimidium Ions from Ketones Promoted by TMSN3/TfOH. J. Org. Chem. 2019, 84, 5603-5613.
  21. Ruengsangtongkul, S.; Chaisan, N.; Thongsornkleeb, C.;* Tummatorn, J.; Ruchirawat, S. Rate Enhancement in CAN-Promoted Pd(PPh3)2Cl2-Catalyzed Oxidative Cyclization: Synthesis of 2-Ketofuran-4-carboxylate Esters. Org. Lett. 2019, 21, 2514-2517. (Selected as an issue’s cover)
  22. 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. 2019, 6, 1340-1355. (Selected as an issue’s cover).
  23. 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.
  24. 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 o-alkynylarylketones via sequential AgTFA-catalyzed ketonization-intramolecular aldol condensation: total synthesis of negundin A. Asian J. Org. Chem. 2018, 7, 932-945.
  25. 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.
  26. Kaewsri, W.; Norseeda, K.; Ruengsangtongkul, S.; Chaisan, N.; hongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. Synthesis of 2-cyclohexenone-2-carboxylate and 4-chloro-2-cyclohexenone-2-carboxylate derivatives via cyclization of alkyne-tethered 1,3-ketoesters. Asian J. Org. Chem. 2018, 7, 203–211.
  27. Chuangsoongnern, P.; Surinrach, C.; Tummatorn, J.;* Thongsornkleeb, C.; Ruchirawat, S. Iodine-mediated cyclization of ortho-alkynylarylketones for the synthesis of indenone derivatives. Eur. J. Org. Chem. 2017, 2017, 5102–5109.
  28. 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.
  29. 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.
  30. 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.
  31. 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.
  32. 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.
  33. 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. Chem. 2015, 94, 56-62.
  34. Tummatorn, J.; Thongsornkleeb, C.; Ruchirawat, S.; Thongarama, P.; Kaewmeea, B. “Convenient and Direct Azidation of sec-Benzyl Alcohols by Trimethylsilyl Azide with Bismuth(III) Triflate Catalyst” Synthesis 2015, 47, 325-329.
  35. 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.
  36. 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.
  37. Tummatorn, J.;* Gleeson, M. P.; Krajangsri, S.; Thongsornkleeb, C.; Ruchirawat, S. “ZrCl4-promoted facile synthesis of indole derivatives” RSC Adv., 2014, 4, 20048–20052.
  38. 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.
  39. 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.
  40. 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.
  41. Radomkit, S.; Sarnpitak, P.; Tummatorn, J.; Batsomboon, P.; Ruchirawat, S.; Ploypradith, P. “Pt(IV)-Catalyzed Generation and [4+2]-Cycloaddition Reactions of o-Quinone Methides” Tetrahedron 2011, 67, 3904-3914.
  42. Tummatorn, J.; Ruchirawat, S.; Ploypradith, P. “A Convergent general strategy for the functionalized 2-aryl cycloalkylfused chromans: Intramolecular Hetero Diels-Alder (HDA) Reactions of ortho-Quinone Methides (o-QMs)” Chem. Eur. J. 2010, 16, 1445-1448.

Other Publications

  1. Tummatorn J, Muñoz GD, Dudley GB. Synthesis of (−)-(R)-angustureine by formal alkynylation of a chiral β-amino ester. Tetrahedron Lett. 2013, 54, 1312-1314.
  2. Tummatorn, J.; Batsomboon, P.; Clark, R. J.; Alabugin, I. V.; Dudley, G. B. “Strain-promoted azide–alkyne cycloadditions of benzocyclononynes” J. Org. Chem. 2012, 77, 2093-2097.
  3. Yang, J.; Tummatorn, J.; Slegeris, R.; Tlasis, S. F.; Dudley, G. B. “Synthesis of the tricyclic core of aldingenin B by oxidative cycloketalization of an alkyne-diol” Org. Lett. 2011, 13, 2065-2067.
  4. Tummatorn, J.; Dudley, G. B. “Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates” Org. Lett. 2011, 13, 1572-1575.
  5. Tummatorn, J.; Dudley, G. B. “Stereospecific formation of homopropargyl amine derivatives by tandem nucleophilic addition/fragmentation of dihydropyridone triflates” Org. Lett. 2011, 13, 158-160.
  6. Tummatorn, J.; Dudley, G. B. “Stereospecific formation of homopropargyl amine derivatives by tandem nucleophilic addition/fragmentation of dihydropyridone triflates” Org. Lett. 2011, 13, 158-160.
  7. Roengsumran, S.; Pata, P.; Ruengraweewat, N.; Tummatorn, J.; Pronpakakul. S.; Sangvanich, P.; Puthong, S.; Petsom, A. “New cleistanthane diterpenoids and 3,4-seco-cleistanthane diterpenoids from Croton oblongifolius” Chem. Nat. Compd. 2009, 45, 641-646.
  8. Tummatorn, J.; Dudley, G. B. “Ring-opening/fragmentation of dihydropyrones for the synthesis of homopropargyl alcohols” J. Am. Chem. Soc. 2008, 130, 5050-5051.
  9. Tummatorn, J.; Albiniak, P. A.; Dudley, G. B. “Synthesis of Benzyl Esters Using 2-Benzyloxy-1 methylpyridinium Triflate” J. Org. Chem. 2007, 72, 8962-8964.
  10. Tummatorn, J.; Khorphueng, P.; Petsom, A.; Muangsin, N.; Chaichit, N.; Roengsumran, S. “Convenient synthetic route to a dehydorotenoid via selective intramolecular aldol condensation of 1,2-diaryl diketone” Tetrahedron 2007, 63, 11878-11885.
  11. Khorphueng, P.; Tummatorn, J.; Petsom, A.; Taylor, R. J. K.; Roengsumran, S. “The total synthesis of 6-deoxyclitoriacetal isolated from Stemona collinase Craib.” Tetrahedron Lett. 2006, 47, 5989-5991.
  12. Khaokum, L.; Sawasdipuksa, N.; Khumthong, N.; Tummatorn, J.; and   Roengsumran, S. “Cardanol Polysulfide as a Vulcanizing Agent for Natural Rubber” J. Sci. Res. 2005, 30, 24-40.

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