Jumreang Tummatorn, Ph.D.

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Affiliation Laboratory of Medicinal Chemistry
Office R614B Chemistry Research Building
Laboratory R619 Chemistry Research Building
Telephone +662-553-8555 Ext. 8812 (Lab)
Fax +662-553-8545
E-mail jumreang@cri.or.th

Education

2002B.Sc. (Chemistry)Burapha University, Thailand
2004M.Sc. (Organic Chemistry)Chulalongkorn University, Thailand
2008Ph.D. (Organic Chemistry)Chulalongkorn University, Thailand
2009-2011Postdoctoral TrainingFlorida State University, USA

Research Interests

We are interested in the rearrangement reaction of azide derivatives and its application to natural product synthesis.

Publications

  1. 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, Article ASAP Full Text
  2. 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. Full Text
  3. 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. Full Text (Selected as an issue's cover)
  4. 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. Full Text (Selected as the issue's front cover)
  5. 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 (Highlighted by Synfacts)
  6. 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
  7. 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
  8. 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
  9. 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
  10. 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
  11. 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
  12. 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
  13. 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
  14. 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
  15. 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
  16. 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
  17. 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
  18. 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
  19. 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
  20. 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
  21. 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.
  22. 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
  23. 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
  24. Tummatorn J, Batsomboon P, Clark RJ, Alabugin IV, Dudley GB.* Strain-promoted azide–alkyne cycloadditions of benzocyclononynes. J. Org. Chem. 2012, 77, 2093-2097.
  25. 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.
  26. Yang J, Tummatorn J, Slegeris R, Tlasis SF, Dudley GB.* Synthesis of the tricyclic core of aldingenin B by oxidative cycloketalization of an alkyne-diol. Org. Lett. 2011, 13, 2065-2067.
  27. Tummatorn J, Dudley GB.* Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates. Org. Lett. 2011, 13, 1572-1575.
  28. Tummatorn J, Dudley GB.* Stereospecific formation of homopropargyl amine derivatives by tandem nucleophilic addition/fragmentation of dihydropyridone triflates. Org. Lett. 2011, 13, 158-160.
  29. Tummatorn J, Ruchirawat S, Ploypradith P.* 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.
  30. 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.
  31. Tummatorn J, Dudley GB.* Ring-opening/fragmentation of dihydropyrones for the synthesis of homopropargyl alcohols. J. Am. Chem. Soc. 2008, 130, 5050-5051.
  32. Tummatorn J, Albiniak PA, Dudley GB.* Synthesis of Benzyl Esters Using 2-Benzyloxy-1 methylpyridinium Triflate. J. Org. Chem. 2007, 72, 8962-8964.
  33. 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.
  34. Khorphueng P, Tummatorn J, Petsom A, Taylor RJK, Roengsumran S.* The total synthesis of 6-deoxyclitoriacetal isolated from Stemona collinase Craib. Tetrahedron Lett. 2006, 47, 5989-5991.
  35. Khaokum L, Sawasdipuksa N, Khumthong N, Tummatorn J, Roengsumran S.* Cardanol Polysulfide as a Vulcanizing Agent for Natural Rubber. J. Sci. Res. 2005, 30, 24-40.

Work Featured on Journal Covers

Students Supervised

Current Thesis Advisees


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

Ms. Bhornrawin Akkachairin
Ph.D. student (2015-Present)

Ms. Pavitra Laohapaisan
Ph.D. Student (2016-Present)

Ms. Nantamon Supantanapong
M.Sc. Student (2016-Present)

Ms. Warabhorn Rodphon
M.Sc. Student (2017-Present)

Current Thesis Co-Advisees

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

Research Assistant


Ms. Pennapa Chuangsoongnern
Research Assistant (2015-Present)

Former Thesis Co-Advisees : Ph.D. Students


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

Former Thesis Co-Advisees : Master Students

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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

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 !!!