Assoc. Prof. Jumreang Tummatorn, Ph.D.

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

1. 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 Full Text (Accepted Manuscripts)
2. 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 Full Text (Accepted Manuscripts)
3. Thongsornkleeb, C.; Tummatorn, J.;* Ruchirawat, S. A Compilation of Synthetic Strategies to Access the Most Utilized Indoloquinoline Motifs. Chem. Asian J. 2022 Full Text (Accepted Articles)
4. 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 Full Text (Early View)
5. 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, Full Text (Early View)
6. 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. Full Text (Selected as an issue’s cover)
7. 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. Full Text
8. Thongsornkleeb, C.; Tummatorn, J.;* Ruchirawat, S. Utilization of ortho-alkynylarylcarbonyl derivatives for creating structurally diverse chemical compounds. Org. Biomol. Chem. 2021, 19, 5982-5998. Full Text
9. 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, 10, 906-917. Full Text
10. 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
11. 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
12. 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
13. 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
14. 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)
15. 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
16. 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
17. 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
18. 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)
19. 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)
20. 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)
21. 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
22. 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
23. 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
24. 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
25. 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
26. 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
27. 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
28. 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
29. 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
30. 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
31. 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
32. 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
33. 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
34. 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
35. 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
36. 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.
37. 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
38. 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
39. Tummatorn J, Batsomboon P, Clark RJ, Alabugin IV, Dudley GB.* Strain-promoted azide–alkyne cycloadditions of benzocyclononynes. J. Org. Chem. 2012, 77, 2093-2097.
40. 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.
41. 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.
42. Tummatorn J, Dudley GB.* Generation of Medium-Ring Cycloalkynes by Ring Expansion of Vinylogous Acyl Triflates. Org. Lett. 2011, 13, 1572-1575.
43. Tummatorn J, Dudley GB.* Stereospecific formation of homopropargyl amine derivatives by tandem nucleophilic addition/fragmentation of dihydropyridone triflates. Org. Lett. 2011, 13, 158-160.
44. 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.
45. 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.
46. Tummatorn J, Dudley GB.* Ring-opening/fragmentation of dihydropyrones for the synthesis of homopropargyl alcohols. J. Am. Chem. Soc. 2008, 130, 5050-5051.
47. Tummatorn J, Albiniak PA, Dudley GB.* Synthesis of Benzyl Esters Using 2-Benzyloxy-1 methylpyridinium Triflate. J. Org. Chem. 2007, 72, 8962-8964.
48. 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.
49. 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.
50. 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 !!!