Assoc. Prof. Jumreang Tummatorn, Ph.D.

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

1. Punjajom, K.; Tummatorn, J.; Ruchirawat, S.; Thongsornkleeb, C.* PdCl2‐Catalyzed Oxidative Cyclization of N‐(2’‐Alkynylaryl)‐1,3‐ketoamides: Synthesis of 3,4‐Diacyl‐2‐Quinolones. Asian J. Org. Chem. 2021 Full Text (Early View)
2. Chaisan, N.; Ruengsangtongkul, S.; Tummatorn, J.; Ruchirawat, S.; Chainok, K.; Thongsornkleeb, C.* Dibrominative Spirocyclization of 2-Butynolyl Anilides: Synthesis of gem-Dibromospirocyclic Benzo[d][1,3]oxazines and Their Application in the Synthesis of 4H-Furo[3,2-b]indoles. J. Org. Chem. 2021, 86, 4671–4698. Full Text
3. 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. Full Text
4. 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. Full Text
5. 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. Full Text
6. Laohapaisan, P.; Chuangsoongnern, P.; Tummatorn, J.;* Thongsornkleeb, C.; Ruchirawat, S. Divergent Synthesis of 3-Hydroxyfluorene and 4-Azafluorene Derivatives from ortho-Alkynylarylketones. J. Org. Chem. 2019, 84, 14451-14460. Full Text (Selected as an issue's cover)
7. Rujimongkon, K.; Mungthin, M; Tummatorn, J.; Ampawong, S.; Adisakwattana, P.; Boonyuen, U.; Reamtong, O.* Proteomic analysis of Plasmodium falciparum response to isocryptolepine derivative. PLOS ONE 2019, 14(8): e0220871. https://doi.org/10.1371/journal.pone.0220871 Full Text
8. 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. Full Text
9. 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
10. 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)
11. 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)
12. 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)
13. 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
14. 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
15. 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
16. 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
17. 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
18. 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
19. 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
20. 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
21. 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
22. 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
23. 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
24. 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
25. 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
26. 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
27. 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
28. 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.
29. 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
30. 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
31. Tummatorn J, Batsomboon P, Clark RJ, Alabugin IV, Dudley GB.* Strain-promoted azide–alkyne cycloadditions of benzocyclononynes. J. Org. Chem. 2012, 77, 2093-2097.
32. 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.
33. 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.
34. Tummatorn J, Dudley GB.* Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates. Org. Lett. 2011, 13, 1572-1575.
35. Tummatorn J, Dudley GB.* Stereospecific formation of homopropargyl amine derivatives by tandem nucleophilic addition/fragmentation of dihydropyridone triflates. Org. Lett. 2011, 13, 158-160.
36. 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.
37. 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.
38. Tummatorn J, Dudley GB.* Ring-opening/fragmentation of dihydropyrones for the synthesis of homopropargyl alcohols. J. Am. Chem. Soc. 2008, 130, 5050-5051.
39. Tummatorn J, Albiniak PA, Dudley GB.* Synthesis of Benzyl Esters Using 2-Benzyloxy-1 methylpyridinium Triflate. J. Org. Chem. 2007, 72, 8962-8964.
40. 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.
41. 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.
42. 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.

• Congratulations to Dr. Wilailak Kaewsri on completing her Ph.D. on June 11, 2018 !!!
• Congratulations to Dr. Krissada Norseeda on completing his Ph.D. on March 28, 2019 !!!
• Congratulations to Dr. Phongprapan Nimnual on completing his Ph.D. on July 26, 2019 !!!