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programs:cb:members:charnsak [2018/09/02 13:51]
charnsak [Oral Presentations]
programs:cb:members:charnsak [2019/03/11 01:33] (current)
charnsak
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 |2006-2008|Postdoctoral Training|City University of New York, NY, USA| |2006-2008|Postdoctoral Training|City University of New York, NY, USA|
  
-===== Research Interests =====+===== Research =====
  
-The current interest of our research lies in the development of new methodology for carbocyclic and heterocyclic intramolecular ring formationsWe are currently investigating the employment of transition metal catalysts, particularly those of noble metals such as gold and platinum complexes, for these processesSubstrates which have been our investigative focus at present are alcohols and amines containing conjugated enyne moiety of various tether lengthsAt 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 complexityThis 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.+| [[https://www.cgi.ac.th/programs/cb/members/charnsak/research_interests|Research Interests]] | [[https://www.cgi.ac.th/programs/cb/members/charnsak/publications|Publications]] | [[https://www.cgi.ac.th/programs/cb/members/charnsak/presentations|Presentations]] | [[https://www.cgi.ac.th/programs/cb/members/charnsak/members|Members]] | [[https://www.cgi.ac.th/programs/cb/members/charnsak/photos|Photos]] | [[https://www.cgi.ac.th/programs/cb/members/charnsak/resources|Resources]] |
  
-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. +<;HTML>
- +<;script src=";https://syndic8.scopus.com/getMessage?registrationId=EEBCFGICEEBCEEBDGECLEHCCFHGDFIJDEJDHFIFDGW&quot;></script
-===== Publications ===== +&lt;/HTML&gt;
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-  - 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.// Articles ASAP. [[https://pubs.acs.org/doi/10.1021/acs.joc.8b01851|Full Text]] +
-  - 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. [[https://onlinelibrary.wiley.com/doi/full/10.1002/ajoc.201800025|Full Text]] +
-  -  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. [[https://www.sciencedirect.com/science/article/pii/S0040403918300261|Full Text]] +
-  - 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. [[http://onlinelibrary.wiley.com/doi/10.1002/ajoc.201700510/full|Full Text]] +
-  - 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. [[http://onlinelibrary.wiley.com/doi/10.1002/ejoc.201700968/full|Full Text]] +
-  - 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. [[http://pubs.acs.org/doi/abs/10.1021/acs.joc.7b00198|Full Text]] +
-  - 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. [[http://pubs.acs.org/doi/abs/10.1021/acs.jafc.6b05697?src=recsys|Full Text]] +
-  - 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. [[http://pubs.rsc.org/en/content/articlelanding/2016/ra/c6ra09396e#!divAbstract|Full Text]]   +
-  - 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. [[http://onlinelibrary.wiley.com/doi/10.1002/ajoc.201600095/abstract|Full Text]] +
-  - 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. [[http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b01305|Full Text]] +
-  - 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. [[http://pubs.acs.org/doi/abs/10.1021/acs.joc.5b00375|Full Text]] +
-  - 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. [[http://www.sciencedirect.com/science/article/pii/S0223523415001439|Full Text]] +
-  - 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. [[https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0034-1379967|Full Text]] +
-  - 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. [[http://pubs.rsc.org/en/Content/ArticleLanding/2014/OB/c4ob00797b#!divAbstract|Full Text]] +
-  - 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. [[https://www.thieme-connect.com/products/ejournals/abstract/10.1055/s-0034-1378225|Full Text]] +
-  - Tummatorn, J.;* Gleeson, M. P.; Krajangsri, S.; **Thongsornkleeb, C.**; Ruchirawat, S. &lt;chem>ZrCl4</chem>-promoted facile synthesis of indole derivatives. //RSC Adv.// **2014**, //4//, 20048–20052. [[http://pubs.rsc.org/en/Content/ArticleLanding/2014/RA/c4ra02158d#!divAbstract|Full Text]] +
-  - 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. [[http://pubs.rsc.org/en/Content/ArticleLanding/2013/OB/c3ob27493d#!divAbstract|Full Text]] +
-  - __**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. [[http://www.sciencedirect.com/science/article/pii/S0040403912017248|Full Text]] +
-  - 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. [[http://www.sciencedirect.com/science/article/pii/S0040402012005224|Full Text]] +
-  - 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. [[http://www.sciencedirect.com/science/article/pii/S0040403911005983|Full Text]] +
-  - 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. [[http://pubs.acs.org/doi/abs/10.1021/jo902172r|Full Text]] +
-  - **Thongsornkleeb, C**.; Danheiser, R. L.* A Practical Method for the Synthesis of 2-Alkynylpropenals. //J. Org. Chem.// **2005**, //70//, 2364–2367. [[http://pubs.acs.org/doi/abs/10.1021/jo047869a|Full Text]] +
-  - 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. [[http://pubs.acs.org/doi/abs/10.1021/ol991342g|Full Text]] +
- +
-===== Presentations ===== +
- +
-==== Oral Presentations ==== +
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-  - 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. +
-  - **Thongsornkleeb, C.** “Efficient and Practical Halogenation Reactions of Organic Compounds” Presented at Chiba University, Chiba, Japan, September 2, 2016. +
-  - **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. +
-  - **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. +
-  - **Thongsornkleeb, C.**; Maibunkaew, T.; Bunrit, A.; Tummatorn, J.; Ruchirawat, S. “Hydrohalogenation and Halogenation by in situ Generation of Reactive Halogenating Species &ampIsocryptolepine Analogues Synthesis and Bioactivities Evaluation” Presented as a part of Asian CORE Program (ACP) Lectureship Tour, Taiwan, March 2–8, 2014. +
-  - **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 ==== +
- +
-  - 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&quotPresented 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. +
-  - **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. +
-  - 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. +
-  - **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. +
-  - **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. +
-  - **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. +
-  - **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. +
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-===== Students Supervised ===== +
- +
-==== Current Thesis Advisees ==== +
-| {{:programs:cb:members:charnsak:krissada_127.jpg?140x190}}\\ **Mr. Krissada Norseeda**\\ Ph.D. student (2014-Present) | {{:programs:cb:members:charnsak:dear.jpg?140x190|}}\\ **Ms. Nattawadee Chaisan**\\ Ph.D. student (2016-Present) | {{:programs:cb:members:charnsak:pang.jpg?140x190|}}\\ **Ms. Kunlayanee Punjajom**\\ M.Sc. student (2017-Present) | +
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-==== Current Thesis Co-Advisees ==== +
-| {{:programs:cb:members:charnsak:s_2981918.jpg?140x190|}}\\ **Mr. Phongprapan Nimnual**\\ Ph.D. student (2014-Present) | +
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-==== Current Research Assistant ==== +
-| {{:programs:cb:members:charnsak:kwang.jpg?140x190|}}\\ **Ms. Sureeporn Ruengsangtongkul**\\ Research Assistant (2015-Present) | +
- +
-==== Former Thesis Advisees : Ph.D. Students ==== +
-| {{:programs:cb:members:charnsak:wilailak_2.jpg?140x190|}}\\ **Dr. Wilailak Kaewsri**\\ Ph.D. student (2013-2018) | +
- +
-==== Former Thesis Advisees : Master Students ==== +
-| {{:programs:cb:members:charnsak:anon_149.jpg?140x190}}\\ **Dr. Anon Bunrit**\\ M.Sc. student (2008-2010) | {{:programs:cb:members:charnsak:wongchak_156.jpg?140x190}}\\ **Dr. Wangchuk Rabten**\\ M.Sc. student (2010-2012) | {{:programs:cb:members:charnsak:tapanee_145.jpg?140x190}}\\ **Ms. Tapanee Maibunkaew**\\ M.Sc. student (2012-2014) | {{:programs:cb:members:charnsak:pasuk_130.jpg?140x190}}\\ **Mr. Pasuk Aroonkit**\\ M.Sc. student (2012-2014) | {{:programs:cb:members:charnsak:piyapratch_160.jpg?140x190}}\\ **Mr. Piyapratch Poonsilp**\\ M.Sc. student (2012-2014) | +
- +
-===== Group Activities and Announcements ===== +
- +
-==== Pizza Time! : July 2015 ==== +
-| {{:programs:cb:members:charnsak:group_activity_1_400.jpg|}} | {{:programs:cb:members:charnsak:group_activity_2_400.jpg|}} | +
- +
-==== Stang's Last Day in the Lab : December 18, 2015 ==== +
-| {{:programs:cb:members:charnsak:s_6430733_400.jpg|}} | +
- +
-==== Congratulations to Dr. Wilailak Kaewsri on completing her Ph.D. on June 11, 2018 !!! ==== +
- +
-===== Great Organic Chemistry Resources on the Internet ===== +
- +
-[[https://www.chem.wisc.edu/areas/reich/group/index.htm|Hans J. Reich (University of Wisconsin)]] +
- +
-[[http://www2.chem.rochester.edu/~nvd/?page=home|Not Voodoo]]+