Seminars - Stockholm University00.pdf · Seminars: Title: “Asymmetric synthesis of lignans” ......

Seminars:

Title:

“Asymmetric synthesis of lignans” Speaker:

Assistant Professor Dr. Darunee Soorukram

and

Title:

“Molecular iodine mediated synthesis of sulfonylindoles and sulfanylindoles”

Speaker: Associate Professor

Dr. Chutima (Kongkittingam) Kuhakarn

From: Faculty of Science, Mahidol University - Thailand

Date: February 5th, 2018 – 3:0 PM – 4:30 PM

Local:

Magnéli

Host: Pher Andersson

Assistant Professor Dr. Darunee Soorukram

ผู้ช่วยศาสตราจารย์ ดร. ดรุณี สู้รักรัมย์

Room: C418B, Department of Chemistry Faculty of Science, Mahidol University Rama 6 Road, Bangkok 10400 Thailand

Phone: +66-(0)2-201-5148; Fax: +66-(0)2-354-7151 E-mail: [email protected]

Education

06/2003 – 12/2006: Dr.rer.nat. (Organic Chemistry), Ludwig-Maximilians-Universität München, Germany (Prof. Dr. Paul Knochel)

06/2000 – 04/2003: M.Sc. (Organic Chemistry), Mahidol University, Bangkok, Thailand (Prof. Dr. Manat Pohmakotr)

1996 – 1999: B.Sc. (Chemistry), Khon Kaen University, Khon Kaen, Thailand

Research and Work Experiences 04/2013 – present: Assistant Professor, Department of Chemistry, Faculty of Science, Mahidol University,

Bangkok, Thailand 05/2009 – 04/2013: Lecturer at Department of Chemistry, Faculty of Science, Mahidol University,

Bangkok, Thailand 10/2007 – 03/2009: Research group leader (Barrett research group), Department of Chemistry, Imperial

College London, England 05/2007 – 03/2009: Postdoctoral researcher with Prof. Dr. Anthony G. M. Barrett at Imperial College

London, England 01/2007 – 03/2007: Postdoctoral researcher with Prof. Dr. Paul Knochel at Ludwig-Maximilians-

Universität München, Germany Research Interests - The development of the fluorination methods - Synthesis of bioactive molecules - Total synthesis of biologically active lignan natural products

List of Publications (2013-2017)

Journal Title 1 Pohmakotr, M.; Kuhakarn, C.; Reutrakul, V.; Soorukram, D.*

Asymmetric Synthesis of Furofurans. Tetrahedron Lett. 2017 (Ahead of Print)

2 Keereewan, S.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.* Fluoride-Catalyzed Nucleophilic Addition of PhSCF2SiMe3 to Isatins: Synthesis of 3-(1',1'-Difluoroalkyl)-3-hydroxyindolin-2-ones.

Eur. J. Org. Chem. 2017 (Ahead of Print)

3 Chaimanee, S.; Pohmakotr, M.; Kuhakarn, C.; Reutrakul, V.; Soorukram, D.* Asymmetric Synthesis of ent-Fragransin C1.

Org. Biomol. Chem. 2017, 15,

39853994.

4 Katrun, P.; Songsichan, T.; Soorukram, D.; Pohmakotr, M.; Reutrakul, V.; Kuhakarn, C.* o-Iodoxybenzoic Acid (IBX)-Iodine Mediated One-Pot Deacylative

Sulfonylation of 1,3-Dicarbonyl Compounds: A Synthesis of β-Carbonyl Sulfones.

Synthesis 49, 2017, 1109-1121.

5 Meesin, J.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Leowanawat, P.; Kuhakarn, C.* Synthesis of N-Alkyl-3-sulfonylindoles and N-Alkyl-3-sulfanylindoles by Cascade Annulation of 2-Alkynyl-N,N-dialkylanilines.


36623669.

6 Hongthong, S.; Meesin, J.; Pailee, P.; Soorukram, D.; Kongsaeree, P.; Prabpai, S.; Piyachaturawat, P.; Jariyawat, S.; Suksen, K.; Jaipetch, T. Nuntasaen, N.; Reutrakul, V.; Kuhakarn, C.* Cytotoxic Lanostanes from Fruits of Garcinia wallichii Choisy (Guttiferae).

Bioorganic Med. Chem. Lett. 2016, 26, 5773-5779.

7 Meesin, J.; Katrun, P.; Reutrakul, V.; Pohmakotr, M.; Soorukram, D.; Kuhakarn, C.* Decarboxylative Sulfonylation of Arylpropiolic Acids with Sulfinic Acids: Synthesis of (E)-Vinyl Sulfones.

Tetrahedron 2016, 72, 1440-1446.

8 Meesin, J.; Katrun, P.; Pareseecharoen, C.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Kuhakarn, C.* Iodine-catalyzed Sulfonylation of Arylacetylenic Acids and Arylacetylenes with Sodium Sulfinates: Synthesis of Arylacetylenic Sulfones.

J. Org. Chem. 2016, 81, 2744-2752.

Journal Title 9 Chumnanvej, N.; Katrun, P.; Pohmakotr, M.; Reutrakul, V.; Soorukram,

D.; Kuhakarn, C.* Nitration-Oximization of Styrene Derivatives with tert-Butyl Nitrite:

Synthesis of α-Nitrooximes.

Chin. J. Chem. 2016, 34, 830-838.

10 Phae-nok, S.; Kuhakarn, C.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.*

Convenient Synthesis of α,β-Unsaturated γ-Butyrolactones and γ-

Butyrolactams via Decarboxylative Iodination of Paraconic Acids and β-

Carboxyl-γ-butyrolactams Using 1,3-Diiodo-5,5-dimethylhydantoin.


1108711095.

11 Srimontree, W.; Masusai, C.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.*

Intramolecular Conjugate Ene Reaction of γ-Difluoromethyl- and γ-

Trifluoromethyl-α,β-Unsaturated γ-Butyrolactones.

J. Org. Chem. 2015, 80,

1051210520.

12 Katrun, P.; Hlekhlai, S.; Meesin, J.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Soorukram, D.; Kuhakarn, C.*

PhI(OAc)2 Mediated Decarboxylative Sulfonylation of β-Aryl-α,β-unsaturated Carboxylic Acids: A Synthesis of (E)-Vinyl Sulfones.


47854795.

13 Phae-nok, S.; Soorukram, D.;* Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M. Silver-Mediated Decarboxylative Fluorination of Paraconic Acids: A

Direct Entry to -Fluorinated -Butyrolactones.

Eur. J. Org. Chem. 2015, 2879-2888.

14 Masusai, C.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Pakawatchai, C.; Saithong, S.; Reutrakul, V.; Pohmakotr, M.* Synthesis of gem-Difluoromethylenated Polycyclic Cage Compounds.

J. Org. Chem. 2015, 80, 1577-1592.

15 Thaharn, W.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Pakawatchai, C.; Saithong, S.; Reutrakul, V.; Pohmakotr, M.* Asymmetric Synthesis of gem-Difluoromethylenated Linear Triquinanes via Cascade gem-Difluoroalkyl Radical Cyclization.

J. Org. Chem. 2015, 80,

816827.

16 Korvorapun, K.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.;

Pohmakotr, M.

Stereoselective Nucleophilic Addition of PhSCF2SiMe3 to Chiral Cyclic Nitrones: Asymmetric Synthesis of gem-Difluoromethylenated Polyhydroxypyrrolizidines and –indolizidines.

Chem. Asian J. 2015, 10, 948-968.

Journal Title 17 Punirun, T.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.*

Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine.

J. Org. Chem. 2015, 80,

79467960.

18 Issaree, A.; Masusai, C.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.*

Synthesis of γ-Difluoromethyl α,β-Un-saturated γ-Butyrolactones Using PhSCF2SiMe3 as a Difluoromethylating Agent.

Eur. J. Org. Chem. 2015, 3751-3759.

19 Hlekhlai, S.; Samakkanad, N.; Sawangphon, T.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Jaipetch, T.; Kuhakarn, C.* Oxone/KI-Mediated Nitration of Alkenes and Alkynes: Synthesis of Nitro-

and β-Iodonitro-Substituted Alkenes.

Eur. J. Org. Chem. 2014,

74337442.

20 Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.*

Synthesis of gem-Difluoromethylenated Compounds Employing ,-

Difluoro--phenylsulfanyl--trimethylsilylmethane (PhSCF2SiMe3) as a gem-Difluoromethylene Building Block.

Synlett 2014, 25, 2558–2573.

21 Chumnanvej, N.; Samakkanad, N.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Soorukram, D.; Kuhakarn, C.*

Convenient synthesis of α-nitrooximes mediated by oxone.

RSC Adv. 2014, 4,

5972659732.

22 Soorukram, D.*; Panmuang, J.; Tuchinda, P.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M. A Stereoselective Approach to Bioactive Secolignans; Synthesis of Peperomin C and Its Analogues.

Tetrahedron 2014, 70,

75777583.

23 Yodwaree, S.; Soorukram, D.*; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M. Formal Synthesis of (+)-3-epi-Epomatilone-6 and the 3,5-Bis-epimer.


68856894.

24 Punirun, T.; Soorukram, D.*; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M. Nucleophilic gem-Difluoro(phenylsulfanyl)methylation of PhSCF2H with Carbonyl Compounds Employing Phosphazene as a Base.


41624169.

25 Katrun, P.; Hongthong, S.; Hlekhlai, S.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Jaipetch, T.; Kuhakarn, C.* Iodine-PPh3-mediated C3-Sulfenylation of Indoles with Sodium Sulfinates.

RSC Adv. 2014, 4,

1893318938.

26 Thaharn, W.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Angew. Chem. Int. Ed. 2014,

Journal Title Pohmakotr, M.* Radical Cyclization/ipso-1,4-Aryl Migration Cascade: Asymmetric Synthesis of 3,3-Difluoro-2-propanoylbicyclo[3.3.0]octanes.

53, 2212 –2215.

27 Katrun, P.; Mueangkaew, C.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Soorukram, D.; Kuhakarn, C.* Regioselective C2 Sulfonylation of Indoles Mediated by Molecular Iodine.

J. Org. Chem. 2014, 79,

17781785.

28 Du-a-man, S.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M.* Synthesis of (+)-Lentiginosine and Its Pyrrolizidine Analogue Based on

Intramolecular Cyclization of α-Sulfinyl Carbanions.


17081715.

29 Masusai, C.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M.*

A synthesis of -trifluoromethyl ,-unsaturated -butyrolactones using CF3SiMe3 as a trifluoromethylating agent.

Org. Biomol. Chem. 2013,

11, 66506658.

30 Masusai, C.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M.* Nucleophilic trifluoromethylation of anhydrides employing

(trifluoromethyl)trimethylsilane: Synthesis of -trifluoromethylated -butyrolactones.

J. Fluorine. Chem. 2013, 154,

3742.

31 Muangkaew, C.; Katrun, P.; Kanchanarugee, P.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Jaipetch, T.; Kuhakarn, C.* PhI(OAc)2/KI mediated acetoxysulfides 1,2-acetoxysulfenylation of

alkenes: facile synthesis of -acetoxysulfides.

Tetrahedron 2013, 69, 8847-8856.

32 Chatupheeraphat, A.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pakawatchai, C.; Saithong, S.; Pohmakotr, M.*

Synthesis of gem-Difluoromethylenated Spiro--butyrolactones Employing PhSCF2TMS as a gem-Difluoromethylenating Agent.


68446858.

33 Pharikronburee, V.; Punirun, T.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M.* Fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to anhydrides: synthesis of gamma-difluoromethylated gamma-lactams.

Org. Biomol. Chem. 2013, 11, 2022-2033.

34 Sawangphon, T.; Katrun, P.; Chaisiwamongkhol, K.; Pohmakotr, M.; Synth. Commun. 2013,

Journal Title Reutrakul, V.; Jaipetch, T.; Soorukram, D.; Kuhakarn, C.* An Improved Synthesis of Vinyl- and -Iodovinyl Sulfones by A Molecular Iodine-Mediated One-pot Iodosulfonation-Dehydroiodination Reaction.

43, 1692-1707.

C. Kuhakarn Page 1 12/15/2017

CURRICULUM VITAE

Name CHUTIMA (KONGKITTINGAM) KUHAKARN (Female, married)

ชุติมา (ก้องกิตติงาม) คูหากาญจน ์

Date of Birth

October 13, 1970, Bangkok, Thailand.

Present Address

Department of Chemistry, Faculty of Science, Mahidol University,

Rama 6 Road, Bangkok 10400, Thailand.

Tel. : 66-0-2201-5395

Fax : 66-0-2354-7151

E-mail : [email protected]

Education

1992 B.Sc., Honors, First Class, Chemistry, Mahidol University, Thailand.

1995 M.Sc., Organic Chemistry, Mahidol University, Thailand.

Research Advisor: Professor Vichai Reutrakul

M.Sc. Thesis: Samarium Iodide Mediated Reduction of -Chloro--

hydroxy Phenyl Sulfoxide Derivatives.

2001 Ph.D., Organic Chemistry, University of Wisconsin, Madison, U.S.A.

Research Advisor: Professor Edwin Vedejs

Dissertation: Synthesis of Sterically Hindered Peptides.

1. Total Synthesis of (-)-Hemiasterlin.

2. Synthesis of the Cyclosporin 8-11 Tetrapeptide

Segment.

Experience

Teaching Assistant Department of Chemistry, Mahidol University, Bangkok,

Thailand, 1994-1995.

Research Assistant Department of Chemistry, University of Michigan, Ann

Arbor, MI, U.S.A., 2001.


Profession

1995-2005 Lecturer, Department of Chemistry, Faculty of Science

Mahidol University.

2005-2012 Assistant Professor, Department of Chemistry, Faculty of Science

Mahidol University.

2012-present Associate Professor, Department of Chemistry, Faculty of

Science, Mahidol University.

Grant Awarded

2002-2003 The Thailand Research Fund: New Researcher Grant

2007 The Thailand Toray Science Foundation: The Awarding of the

Science and Technology Grants

2008-2011 The Thailand Research Fund: Research Grant for Mid-career

University Faculty

2011-2014 The Thailand Research Fund: TRF Research Scholar

2015-2018 The Thailand Research Fund: TRF Advanced Research Scholar

Publications 1. “Synthesis of C2-symmetric gem-difluoromethylenated angular triquinanes”

Thaharn, W.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.*

J. Org. Chem. 2017, DOI: 10.1021/acs.joc.7b02777.

2. “Synthesis of difluoromethyl ketones from Weinreb amides, and tandem

addition/cyclization of o-alkynylaryl Weinreb amides” Phetcharawetch, J.;

Betterley, N. M.; Soorukram, D.; Pohmakotr, M.; Reutrakul, V.; Kuhakarn,

C.* Eur. J. Org. Chem. 2017, DOI: 10.1002/ejoc.201701322.

3. “TBAI/TBHP-mediated cascade cyclization toward sulfonylated indeno[1,2-

c]quinolones” Meesin, J.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.;

Leowanawat, P.; Saithong, S.; Kuhakarn, C.* Org. Lett. 2017, 19, 6546-

6549.

4. “Asymmetric synthesis of furofurans” Pohmakotr, M.; Kuhakarn, C.;

Reutrakul, V.; Soorukram, D.* Tetrahedron Lett. 2017,

https://doi.org/10.1016/j.tetlet.2017.11.011

5. “Antibiofilm activity of α-mangostin extracted from Garcinia mangostana

L. against Staphylococcus aureus” Nguyen, T. M. P.*; Ngo, V. Q.; Ta, T.


M.; Nguyen, V. A.; Kuhakarn, C.; Reutrakul, V.; Bolhuis, A. Asian Pac. J.

Trop. Med. 2017, https://doi.org/10.1016/j.apjtm.2017.10.022.

6. “Fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to isatins:

Synthesis of 3-(1′,1′-difluoroalkyl)-3-hydroxyindolin-2-ones” Keereewan,

S.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.* Eur. J.

Org. Chem. 2017, DOI: 10.1002/ejoc.201701106.

7. Pailee P.; Kruahong, T.; Hongthong, S.; Kuhakarn, C.; Jaipetch, T.;

Pohmakotr, M.; Jariyawat, S.; Suksen, K.; Akkarawongsapat, R.;

Limthongkul, J.; Panthong, A.; Kongsaeree, P.; Prabpai, S.; Tuchinda, P.;

Reutrakul, V.* Phytochem. Lett. 2017, 20, 111-118.

8. “Cytotoxic, anti-HIV-1 and anti-inflammatory activities of lanostanes from

fruits of Garcinia speciosa” Pailee P.; Kruahong, T.; Hongthong, S.;

Kuhakarn, C.; Jaipetch, T.; Pohmakotr, M.; Jariyawat, S.; Suksen, K.;

Akkarawongsapat, R.; Limthongkul, J.; Panthong, A.; Kongsaeree, P.;

Prabpai, S.; Tuchinda, P.; Reutrakul, V.* Phytochem. Lett. 2017, 20, 111-

118.

9. “Asymmetric synthesis of ent-fragransin C-1” Chaimanee, S.; Pohmakotr,

M.; Kuhakarn, C.; Reutrakul, V.; Soorukram, D.* Org. Biomol.

Chem. 2017, 15, 3985-3994.

10. “Synthesis of N-alkyl-3-sulfonylindoles and N-alkyl-3-sulfanylindoles by

cascade annulation of 2-alkynyl-N,N-dialkylanilines” Meesin, J.; Pohmakotr,

M.; Reutrakul, V.; Soorukram, D.; Leowanawat, P.; Kuhakarn, C.* Org.

Biomol. Chem. 2017, 15, 3662-3669.

11. “o-Iodoxybenzoic acid (IBX)-iodine mediated one-pot deacylative

sulfonylation of 1,3-dicarbonyl compounds: A synthesis of β-carbonyl

sulfones” Katrun, P.; Songsichan, T.; Soorukram, D.; Pohmakotr, M.;

Reutrakul, V.; Kuhakarn, C.* Synthesis 2017, 49, 1109-1121.

12. “Cytotoxic lanostanes from fruits of Garcinia wallichii Choisy (Guttiferae)”

Hongthong, S.; Meesin, J.; Pailee, P.; Soorukram, D.; Kongsaeree, P.;

Prabpai, S.; Piyachaturawat, P.; Jariyawat, S.; Suksen, K.; Jaipetch, T.;

Nuntasaen, N.; Reutrakul, V.; Kuhakarn, C.* Bioorg. Med. Chem. Lett.

2016, 26, 5773-5779.

13. “Organopromoted direct synthesis of 1,1-diphenyl-3-arylindanes via formal

[3+2] cycloadditions of triphenylcarbenium tetrafluoroborate with styrenes”


Surapanich, N.*; Chaisuwan, P.; Kuhakarn, C.; Reutrakul, V. Synlett 2016,

27, 2689-2694.

14. “A new neolignan, and the cytotoxic and anti-HIV-1 activities of

constituents from the roots of Dasymaschalon sootepense” Hongthong, S.;

Kuhakarn, C.*; Jaipetch, T.; Piyachaturawat, P.; Jariyawat, S.; Suksen, K.;

Limthongkul, J.; Nuntasaen, N.; Reutrakul, V. Nat. Prod. Commun. 2016,

11, 809-813.

15. “Nitration-oximization of styrene derivatives with tert-butyl nitrite: synthesis

of α-nitrooximes” Chumnanvej, N.; Katrun, P.; Pohmakotr, M.; Reutrakul,

V.; Soorukram, D.; Kuhakarn, C.* Chin. J. Chem. 2016, 34, 830-838.

16. “Iodine-catalyzed sulfonylation of arylacetylenic acids and arylacetylenes

with sodium sulfinates: synthesis of arylacetylenic sulfones” Meesin, J.;

Katrun, P.; Pareseecharoen, C.; Pohmakotr, M.; Reutrakul, V.; Soorukram,

D.; Kuhakarn, C.* J. Org. Chem. 2016, 81, 2744-2752.

17. “Decarboxylative sulfonylation of arylpropiolic acids with sulfinic acids:

synthesis of (E)-vinyl sulfones” Meesin, J.; Katrun, P.; Reutrakul, V.;

Pohmakotr, M.; Soorukram, D.; Kuhakarn, C.* Tetrahedron 2016, 72,

1440-1446.

18. “Intramolecular conjugate ene reaction of -difluoromethyl- and -

trifluoromethyl-,β-unsaturated -Butyrolactones” Srimontree, W.; Masusai,

C.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.* J. Org.

Chem. 2015, 80, 10512-10520.

19. “Polyoxygenated cyclohexene derivatives isolated from Dasymaschalon

sootepense and their biological activities” Hongthong, S.; Kuhakarn, C.*;

Jaipetch, T.; Prabpai, S.; Kongsaeree, P.; Piyachaturawat, P.; Jariyawat, S.;

Suksen, K.; Limthongkul, J.; Panthong, A.; Nuntasaen, N.; Reutrakul, V.

Fitoterapia 2015, 106, 158-166.

20. “Silver-mediated decarboxylative fluorination of paraconic acids: A direct

entry to -fluorinated -butyrolactones” Phae-nok, S.; Kuhakarn, C.;

Pohmakotr, M.; Reutrakul, V.; Soorukram, D.* Org. Biomol.

Chem. 2015, 13, 11087-11095.

21. “Stereoselective Synthesis of 1-Fluoro-exo,exo-2,6-diaryl-3,7-

dioxabicyclo[3.3.0]octanes: Synthesis of (±)-1-Fluoromembrine” Punirun,


T.; Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.* J. Org.

Chem. 2015, 80, 7946-7960.

22. “PhI(OAc)2 mediated decarboxylative sulfonylation of β-aryl-α,β-

unsaturated carboxylic acids: A synthesis of (E)-vinyl sulfones” Katrun, P.;

Hlekhlai, S.; Meesin, J.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.;

Soorukram, D.; Kuhakarn, C.* Org. Biomol. Chem. 2015, 13, 4785-4794.

23. “Synthesis of γ-difluoromethyl α,β-unsaturated γ-butyrolactones using

PhSCF2SiMe3 as a difluoromethylating agent” Issaree, A.; Masusai, C.;

Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.* Eur. J. Org.

Chem. 2015, 3751-3759.

24. “A general direct arylation of polyfluoroarenes with heteroaryl and aryl

chlorides catalyzed by palladium indolylphosphine complexes” Yuen, O. Y.;

Mueangkaew, C. So, C. M.; Kuhakarn, C.; Kwong, F. Y.* Chem. An Asian

J. 2015, 10, 857-861.

25. “Stereoselective nucleophilic addition of PhSCF2SiMe3 to chiral cyclic

nitrones: Asymmetric synthesis of gem-difluoromethylenated

polyhydroxypyrrolizidines and –indolizidines” Korvorapun, K.; Soorukram,

D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M.* Chem. An

Asian J. 2015, 10, 948-968.

26. “Silver-mediated decarboxylative fluorination of paraconic acids: A direct

entry to β-fluorinated γ-butyrolactones” Phae-nok, S.; Soorukram, D.*;

Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M. Eur. J. Org. Chem. 2015,

2879-2888.

27. “Asymmetric synthesis of gem-difluoromethylenated linear triquinanes via

cascade gem-difluoroalkyl radical cyclization” Thaharn, W.; Soorukram, D.;

Kuhakarn, C.; Tuchinda, P.; Pakawatchai, C.; Saithong, S.; Reutrakul, V.

Pohmakotr, M.* J. Org Chem. 2015, 80, 816-827.

28. “Synthesis of gem-Difluoromethylenated Polycyclic Cage Compounds”

Masusai, C.; Soorukram, D.; Kuharkarn, C.; Tuchinda, P.; Pakawatchai,

C.; Saithong, S.; Reutrakul, V.; Pohmakotr, M.* J. Org Chem. 2015, 80,

1577-1592.

29. “OXONE®/KI-Mediated Nitration of Alkenes and Alkynes: Synthesis of

Nitroalkenes and β-Iodonitroalkenes” Hlekhlai, S.; Samakkanad, N.;


Sawangphon, T.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Jaipetch, T.;

Kuharkarn, C.* Eur. J. Org. Chem. 2014, 7433-7442.

30. “Convenient Synthesis of α-Nitrooximes Mediated by OXONE®”

Chumnanvej, N.; Samakkanad, N.; Pohmakotr, M.; Reutrakul, V.; Jaipetch,

T.; Soorukram, D.; Kuharkarn, C.* RSC Adv. 2014, 4, 59726-59732.

31. “Synthesis of gem-Difluoromethylenated Compounds Employing α,α-

Difluoro-α-phenylsulfanyl-α-trimethylsilylmethane (PhSCF2SiMe3) as a

gem-Difluoromethylene Building Block” Soorukram, D.; Kuharkarn, C.;

Reutrakul, V.; Pohmakotr, M.* Synlett 2014, 25, 2558-2573.

32. “Cytotoxic alkaloids from leaves and twigs of Dasymaschalon sootepense”

Hongthong, S.; Kuhakarn, C.; Reutrakul, V., Jariyawat, S.; Piyachaturawat,

P.; Nuntasaen, N.; Jaipetch, T.* Nat. Prod. Commun. 2014, 9, 929-932.

33. “A stereoselective approach to bioactive secolignans: synthesis of peperomin

C and its analogues” Soorukram, S.*; Panmuang, J.; Tuchinda, P.;

Kuhakarn, C.; Reutrakul, V.; Pohmakotr. M. Tetrahedron 2014, 70, 7577-

7583.

34. “Formal synthesis of (+)-3-epi-eupomatilone-6 and the 3,5-bis-epimer”

Yodwaree, S.; Soorukram, D.*; Kuhakarn, C.; Tuchinda, C.; Reutrakul, V.;

Pohmakotr, M. Org. Biomol. Chem. 2014, 12, 6885-6894.

35. “Nucleophilic gem-difluoro(phenylsulfanyl)methylation of carbonyl

compounds with PhSCF2H in the presence of a phosphazene as a base”

Punirun, T.; Soorukram, D.*; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.

Eur. J. Org. Chem. 2014, 4162-4169.

36. “Iodine-PPh3-mediated C3-sulfenylation of indoles with sodium sulfinates”

Katrun, P.; Hongthong, S.; Hlekhlai, S.; Pohmakotr, M.; Reutrakul, V.;

Soorukram, D.; Jaipetch, T.; Kuhakarn, C.* RSC Adv. 2014, 4, 18933-

18938.

37. “Regioselective C2 sulfonylation of indoles mediated by molecular iodine”

Katrun, P.; Mueangkaew, C.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.;

Soorukram, D.; Kuhakarn, C.* J. Org. Chem. 2014, 79, 1778-1785.

38. “Radical cyclization/ipso-1,4-aryl migration cascade: Asymmetric synthesis

of 3,3-difluoro-2-propanoylbicyclo[3.3.0]octanes” Thaharn, W.; Soorukram,

D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M.* Angew.

Chem, Int. Ed. 2014, 53, 2212-2215.


39. “Synthesis of (+)-lentiginosine and its pyrrolizidine analogue based on

intramolecular cyclization of α-sulfinyl carbanions” Du-a-man, S.;

Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr,

M.* Eur. J. Org. Chem. 2014, 1708-1715.

40. “Electrophilic difluoro(phenylthio)methylation: Generation, stability, and

reactivity of α-fluorocarbocations” Betterley, N. M.; Surawatanawong, P.;

Prabpai, S.; Kongsaeree, P.; Kuhakarn, C.; Pohmakotr, M.; Reutrakul. V.*

Org. Lett. 2013, 15, 5666-5669.

41. “A synthesis of gamma-trifluoromethyl α,β-unsaturated -butyrolactones

using CF3SiMe3 as a trifluoromethylating agent” Masusai, C.; Soorukram,

D.; Kuhakarn, C.; Tuchinda, P.; Pakawatchai, C.; Saithong, S.; Reutrakul,

V.; Pohmakotr. M.* Org. Biomol. Chem. 2013, 11, 6650-6658.

42. “Synthesis of gem-difluoromethylenated spiro--butyrolactones by

employing PhSCF2Si(CH3)3 as a gem-difluoromethylenating agent”

Chatupheeraphat, A.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.;

Reutrakul, V.; Pakawatchai, C.; Saithong, S.; Pohmakotr, M.* Eur. J. Org.

Chem. 2013, 6844-6858.

43. “PhI(OAc)2/KI mediated 1,2-acetoxysulfenylation of alkenes: Facile

synthesis of β-acetoxysulfides” Muangkaew, C.; Katrun, P.; Kanchanarugee,

P.; Pohmakotr, M.; Reutrakul, V.; Soorukram, D.; Jaipetch, T.; Kuhakarn,

C.* Tetrahedron 2013, 69, 8847-8856.

44. “Nucleophilic trifluoromethylation of anhydrides employing

(trifluoromethyl)trimethylsilane: Synthesis of -trifluoromethylated -

butyrolactones” Masusai, C.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.;

Reutrakul, V.; Pohmakotr, M.* J. Fluorine Chem. 2013, 154, 37-42.

45. “Fluoride-catalyzed nucleophilic addition of PhSCF2SiMe3 to anhydrides:

Synthesis of -difluoromethylated -lactams” Pharikronburee, V.; Punirun,

T.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr,

M.* Org. Biomol. Chem. 2013, 11, 2022-2033.

46. “An improved synthesis of vinyl- and -iodovinyl sulfones by a molecular

iodine-mediated one-pot iodosulfonation-dehydroiodination reaction”

Sawangphon, T.; Katrun, P.; Chaisiwamongkhol, K.; Pohmakotr, M.;


Reutrakul, V.; Pohmakotr; M.; Jaipetch; T.; Soorukram; D.; Kuhakarn, C.*

Synth. Commun. 2013, 43, 1692-1707.

47. “The Morita-Baylis-Hillman reaction of chiral highly oxygenated cyclopent-

2-enones” Masusai, C.; Soorukram, D.; Kuhakarn, C.; Tuchinda, P.;

Pakawatchai, C.; Reutrakul, V.; Pohmakotr, M.* Helv. Chim. Acta 2012, 95,

1912-1927.

48. “Palladium-mediated Heck-type reactions of

[(bromodifluoromethyl)sulfonyl]benzene: Synthesis of α-alkenyl- and α-

heteroaryl-substituted α,α-difluoromethyl phenyl sulfones” Surapanich, N.;

Kuhakarn, C.; Pohmakotr, M.; Reutrakul, V.* Eur. J. Org. Chem. 2012,

5943-5952.

49. “Reactions of the vicinal dianion of di-(-)-menthyl succinate with carbonyl

compounds and benzyl bromide” Soorukram, D.*; Yodwaree, S.; Tuchinda,

P.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M. Arkivoc 2012, ix, 21-34.

50. “Asymmetric synthesis of gem-difluoromethylenated

dihydroxypyrrolizidines and Indolizidines” Thaharn, W.; Bootwicha, T.;

Soorukram, D.; Kuhakarn, C.; Prabpai, S.; Kongsaeree, P.; Tuchinda, P.;

Reutrakul, V.; Pohmakotr, M.* J. Org. Chem. 2012, 77, 8465-8479.

51. “IBX/I2-mediated reaction of sodium arenesulfinates with alkenes: facile

synthesis of β-keto sulfones” Samakkanad, N.; Katrun, P.; Techajaroonjit,

T.; Hlekhlai, S.; Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Soorukram, D.;

Kuhakarn, C.* Synthesis 2012, 44, 1693-1699.

52. “Synthesis of gem-difluoromethylenated bicyclo[m.n.0]alkan-1-ols and their

ring-expansion to gem-difluoromethylenated macrocyclic lactones” Punirun,

T.; Peewasan, K.; Kuhakarn, C.; Soorukram, D.; Tuchinda, P.; Reutrakul,

V.; Kongsaeree, P.; Prabpai, S.; Pohmakotr, M.* Org. Lett. 2012, 14, 1820-

1823.

53. “Studies toward the total synthesis of naturally occurring

pyranonaphthoquinones from Ventilago harmandiana” Kongsriprapan, S.;

Kuhakarn, C.; Deelertpaiboon, P.; Panthong, K.; Tuchinda, P.; Pohmakotr,

M.; Reutrakul V.* Pure Appl. Chem. 2012, 84, 1435-1443.

54. “Prenylated caged xanthones: Chemistry and biology” Anantachoke, N.;

Tuchinda, P.; Kuhakarn, C.; Pohmakotr, M.; Reutrakul, V.*

Pharmaceutical Biology, 2012, 50(1), 78-91.


55. “α,α-Difluoro-α-phenylsulfanyl-α-trimethylsilylmethane as "●CF2

-" synthetic

building block for the preparation of gem-difluoromethylenated

cyclopentanols” Peewasan, K.; Kuhakarn, C.; Soorukram, D.; Tuchinda, P.;

Reutrakul, V.; Pohmakotr, M.* J. Fluorine Chem. 2012, 135, 367-372.

56. “Friedel–Crafts-type alkylation with bromodifluoro(phenylsulfanyl)methane

through -fluorocarbocations: Syntheses of thioesters, benzophenones and

xanthones” Kuhakarn, C.; Surapanich, N.; Kamtonwong, S.; Pohmakotr,

M.; Reutrakul V.* Eur. J. Org. Chem. 2011, 5911-5918.

57. “Asymmetric total synthesis of (+)-swainsonine” Chooprayoon, S.;

Kuhakarn, C.; Tuchinda, P.; Reutrakul, V.; Pohmakotr, M.* Org. Biol. Mol.

Chem. 2011, 531-537.

58. “PhI(OAc)2/KI-mediated reaction of aryl sulfinates with alkenes, alkynes,

and ,β-unsaturated carbonyl compounds: Synthesis of vinyl sulfones and β-

iodovinyl sulfones” Katrun, P.; Chiampanichayakul, S.; Korworapan, K.;

Pohmakotr, M.; Reutrakul, V.; Jaipetch, T.; Kuhakarn, C.* Eur. J. Org.

Chem. 2010, 5633-5641.

59. “Synthesis of (+)-4-desoxypentenomycin and analogs” Kambutong, S.;

Kuhakarn, C.; Tuchinda, P.; Pohmakotr, M.* Synthesis 2010, 1453-1458.

60. “Facile oxidative hydrolysis of acetals to esters using hypervalent

iodine(III)/LiBr combination in water” Panchan, W.; Chiampanichayakul,

S.; Snyder, D. L.; Yodbuntung, S.; Pohmakotr, M.; Reutrakul, V.; Jaipetch,

T.; Kuhakarn, C.* Tetrahedron 2010, 66, 2732-2735.

61. “Efficient synthesis of alkyl 2,3-unsaturated glucopyranosides from glycals

mediated by ytterbium(III) triflate-trialkyl aluminum” Deelertpaiboon, P.;

Reutrakul, V.*; Jarussophon, S.; Tuchinda, P.; Kuhakarn, C.; Pohmakotr,

M. Tetrahedron Lett. 2009, 50, 6233-6235.

62. “A synthetic strategy to pyrrolidines and piperidines based on cyclization of

-sulfinyl carbanions” Sakulsaknimitr, W.; Kuhakarn, C.; Tuchinda, P.;

Reutrakul, V.; Pohmakotr, M.* Arkivoc 2009, xii, 81-97.

63. “Fluoride-catalyzed addition of PhSCF2SiMe3 to N-substituted cyclic imides

followed by radical cyclization: General synthetic strategy of gem-

difluoromethylenated 1-azabicyclic compounds” Bootwicha, T.; Panichakul,

http://apps.isiknowledge.com/full_record.do?product=WOS&search_mode=GeneralSearch&qid=1&SID=U1FLGkI1PnD@K8HC2A@&page=1&doc=1





D.; Kuhakarn, C.; Prabpai, S.; Kongsaeree, P.; Tuchinda, P.; Reutrakul, V.;

Pohmakotr, M.* J. Org. Chem. 2009, 74, 3798-3805.

64. “2-Iodoxybenzoic acid/tetraethylammonium bromide/water: An efficient

combination for oxidative cleavage of acetals” Kuhakarn, C.*; Panchan,

W.; Chiampanichayakul, S.; Samakkanad, N.; Pohmakotr, M.; Reutrakul, V.;

Jaipetch, T. Synthesis 2009, 929-934.

65. “Oxidative conversion of amines into their corresponding nitriles using o-

iodoxybenzoic acid (IBX)/iodine: selective oxidation of aminoalcohols to

hydroxynitriles” Chiampanichayakul, S.; Pohmakotr, M.; Reutrakul, V.;

Jaipetch, T.; Kuhakarn, C.* Synthesis 2008, 2045-2048.

66. “Asymmetric synthesis of pentenomycin I, epipentenomycin I and their

analogs” Pohmakotr, M.;* Kambutong, S.; Tuchinda, P.; Kukakarn, C.

Tetrahedron 2008, 64, 6315-6323.

67. “Synthesis of alkylated indolizidine alkaloids via Pummerer mediated

cyclization: synthesis of (±)-indolizidine 167B, (±)-5-butylindolizidine and

(±)-monomorine I” Kuhakarn, C.*; Phachanee, S.; Jaipetch, T.; Pohmakotr,

M.; Reutrakul, V. Tetrahedron 2008, 64, 1663-1670.

68. “A variation of the Pictet-Spengler reaction via a sequential reduction-

cyclization reaction of N-acylcarbamate: Synthesis of 1-substituted

tetrahydroquinoline derivatives” Kuhakarn, C.*; Panyachariwat, N.;

Ruchirawat, S.* Tetrahedron Lett. 2007, 48, 8182-8184.

69. “Highly diastereoselective synthesis of -carboxy--lactams and their ethyl

esters via Sc(OTf)3-catalyzed imino Mukaiyama-aldol type reaction of 2,5-

bis(trimethylsilyloxy)furan with imines” Pohmakotr, M.*; Yotapan, N.;

Tuchinda, P.; Kuhakarn, C.; Reutrakul, V. J. Org. Chem. 2007, 72, 5016-

5019.

70. “Lanthanide triflate catalyzed generation of N-acyliminium ions from -

amido sulfones: the synthesis of (1-alkyl-1-aryl)methyl phenyl sulfones”

Kuhakarn, C.; Tangdenpaisal, K.; Kongsaeree, P.; Prabpai, S.; Tuchinda,

P.; Pohmakotr, M.*; Reutrakul, V.* Tetrahedron Lett. 2007, 48, 2467-2470.

71. “Stereoselective synthesis of -carboethoxy--lactams via imino Mukaiyama

aldol-type reaction of 1,4-bis(trimethylsilyloxy)-1,4-diethoxy-1,3-butadiene”


Pohmakotr, M.;* Yotapan, N.; Tuchinda, P.; Kuhakarn, C.; Reutrakul, V.*

Tetrahedron 2007, 63, 4328-4337.

72. “Mild oxidation of alcohols with o-iodoxybenzoic acid (IBX) in

water/CH2Cl2 mixture in the presence of phase-transfer catalyst” Kuhakarn,

C.*; Kittigowittana, K.; Ghabkham, P.; Pohmakotr, M.; Reutrakul, V. Synth.

Commun. 2006, 36, 2887-2892.

73. “Samarium dienolate mediated stereoselective synthesis of anti-1,3-diol

monoesters via aldol-Tishchenko reaction” Reutrakul, V.*;

Jaratjaroonphong, J.; Tuchinda, P.; Kuhakarn, C.; Kongsaeree, P.; Prabpai,

S.; Pohmakotr, M.* Tetrahedron Lett. 2006, 47, 4753-4757.

74. “IBX/n-Bu4NBr/CH2Cl2-H2O: a new mild system for selective oxidation of

secondary alcohols” Kuhakarn, C.*; Kittigowittana, K.; Pohmakotr, M.;

Reutrakul, V. Tetrahedron 2005, 61, 8995-9000.

75. “Investigation of substrate-selectivity pattern in the oxidation of secondary

alcohols by amino acid-derived IBX derivatives” Kuhakarn, C.*;

Kittigowittana, K.; Pohmakotr, M.; Reutrakul, V. ARKIVOC 2005 (i), 143-

153.

76. “Difluorophenylsulfanylmethyl radical and difluoromethylene diradical

synthons: gem-difluoromethylene building block” Reutrakul, V.*;

Thongpaisanwong, T.; Tuchinda, P.; Kuhakarn, C.; Pohmakotr, M.* J. Org.

Chem. 2004, 69, 6913-6915.

77. “A total synthesis of (-)-hemiasterlin using N-Bts methodology” Vedejs, E.*;

Kongkittingam, C. J. Org. Chem. 2001, 66, 7355-7364.

78. “Solution-phase synthesis of a hindered N-methylated tetrapeptide using Bts-

protected amino acid chlorides: efficient coupling and methylation steps

allow purification by extraction” Vedejs, E.*; Kongkittingam, C. J. Org.

Chem. 2000, 65, 2309-2318.

Book

“Catalysts for Fine Chemical Synthesis Vol. 5: Regio- and Stereo- Controlled Oxidation

and Reductions” 5.3 2-IODOXYBENZOIC ACID (IBX)/n-Bu4NBr/CH2Cl2-H2O: A

MILD SYSTEM FOR SELECTIVE OXIDATION OF SECONDARY ALCOHOLS,

Krisada Kittigowittana, Manat Pohmakotr, Vichai Reutrakul and Chutima Kuhakarn;

edited by S. Roberts and J. Whittall © 2007 John Wiley & Sons, Ltd


Reviews

Soorukram, D.; Kuhakarn, C.; Reutrakul, V.; Pohmakotr, M.* Benzene,

[[difluoro(trimethylsilyl)methyl]thio]-. Encyclopedia of Reagents for Organic Synthesis

2011.

Kuhakarn, C.; Pohmakotr, M.; Reutrakul, V.* Bromodifluorophenylsulfanylmethane.

Encyclopedia of Reagents for Organic Synthesis 2007.

Presentations

1) Kuhakarn, C.; Chiampanichayakul, S.; Panchan, W.; Pohmakotr, M.; Reutrakul, V.;

Jaipetch, T. New Synthetic Applications of o-Iodoxybenzoic Acid (IBX) in Organic

Synthesis. The 4th

International Conference on Cutting-Edge Organic Chemistry in

Asia, Poster conference, Bangkok, Thailand, 28 November-3 December 2009,

Lectureship Award to visit Japan in 2010.

2) Kuhakarn, C.; Seehasombat, P.; Pohmakotr, M.; Reutrakul, V. Application of

intramolecular Pummerer reaction: synthesis of alkylated indolizidine alkaloids.

Contemporary Organic Synthesis Symposium, UK-Thailand Partners in Science,

National Science and Technology Development Agency (NSTDA), Pathumthani,

Thailand, 22 February 2008, Invited Lecture.

3) Kuhakarn, C.; Seehasombat, P.; Pohmakotr, M.; Reutrakul, V. Synthesis of

alkylated indolizidine alkaloids via Pummerer mediated cyclization. International

Symposium on Catalysis and Fine Chemical 2007 (C&FC2007), Poster conference,

Nanyang Technological University, Singapore, 16-21 December 2007. (Poster award)

4) Kuhakarn, C.; Kittigowittana, K.; Pohmakotr, M.; Reutrakul, V. Chemoselectivity

in IBX mediated oxidation of alcohols to carbonyl compounds. The 1st International

Conference on Cutting-Edge Organic Chemistry in Asia, Poster conference, Okinawa,

Japan, 16-20 October 2006.

Research Interest

Bioassay-guided isolation of natural products from plants.

Development of new synthetic methodologies for organic synthesis.

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