Prof. Sangho Koo

       Tel :82-31-330-6185, Fax : 82-31-335-7248

       e-mail : sangkoo@mju.ac.kr

Education
   1985: B.S.   Seoul National University, Chemistry Major
   1987: M.S.  The University of Michigan, Organic Chemistry
   1992: Ph. D. (Professor Masato Koreeda), The University of Michigan, Organic Chemistry
   1992 - 1994: Post-doctoral Fellow Emory University


Professional Career
    
1992 -  1994: Post-doctoral Fellow (Professor Lanny Liebeskind), Emory University
    1994 -  1998: Assistant Professor in Chemistry, Myong Ji University
    1998 -  1999: Chairman of Chemistry Department, Myong Ji University
    1998 -  2002: Associate Professor in Chemistry, Myong Ji University
    2006 -  2013: Professor in Nano Science and Engineering, Myong Ji University
    2003 -  present: Full Professor in Chemistry, Myong Ji University
    2006 -  present: Special Visiting Professor, School of Pharmacy East China University of Science and Technology,
                            Shanghai, China
   2013 - present: Professor in Energy and Bioengeneering, Myong Ji University

 

Research Areas

  1. Development of Efficient Cyclization Methods: We are interested in efficient and practical syntheses of cyclic ,-unsaturated carbonyl compounds that can be served as versatile building blocks for the synthesis of polycyclic natural products. Efficient synthetic methods for the following compounds have been developed, and the syntheses of polycyclic structures by use of those compounds are under investigation.         1) Cyclohexenones
            2) Cyclopentenones
            3) Cycloalkene-1-carboxaldehydes
            4) Bicyclo[3.3.1]nonanes
            5) D1-3-Octalones

  2. Chemistry of Isoprenoid: Isoprenoid can be classified into Terpenoid, Carotenoid, and Steroid. We have developed various di-functionalized C5 prenyl units that can be efficiently used in chain-extension processes for making various Isoprenoid compounds. We adopted Julia Sulfone protocol in C-C bond formation, which would give polyprenyl or polyene structures depending on the sulfone elimination process.  Carotenoid natural products have been nicely assembled by use of our C10 di(chloroallylic) sulfide.  We are currently extending this strategy to make other important carotenoid compounds.  After finishing up the synthesis of carotenoid compounds, we will further pursue the synthesis of terpenoid and steroid compound by combined use of our cyclization and chain-extension strategies.  Followings are the carotenoid compounds that we have made or have been making at the present time.

       1) Vitamin A                                 8) Crocetin
       2) Tretinoin                                   9) Nor-Bixin
       3) Isotretinoin                               10) Zeaxanthin
       4) Tocoretinate                             11) Asthaxanthin
       5) b-carotene                               12) Canthaxanthin
       6) Retinyl sulfide                          13) Coenzyme Q-10
       7) Lycopene                                14) Biotin

   


Research Paper List (since 1995)

1,2-addition of Dimethyl(phenyl)silyllithium to Cyclic a,b-Unsaturated Ketones and Regiospecific Generation of Cyclic Silyl Enol Ethers through Brook Rearrangement of the1,2-AdditionProducts, Koreeda,M.;Koo,S. Tetrahedron Lett. 1990, 31, 831.

A General Synthetic Entry to Highly-Oxygenated, Angularly-Fused Polycyclic Aromatic Compound. Koo, S.; Liebeskind, L. J. Am. Chem. Soc. 1995, 117, 3389.

Allyl Trifluoromethanesulfonate, Koo, S. Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed, Wiley, London, 1995, vol 1, pp 130.

Thallium(I) Acetate, Koo, S. Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed, Wiley, London, 1995, vol 7, pp 4832.

N-Phenylcampholylhydroxamic Acid, Koo, S. Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed, Wiley, London, 1995, vol 6, pp 3965.

Bis(N-propylsalicylideneiminato)cobalt, Koo, S. Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed, Wiley, London, 1995, vol 1, pp 552.

3-Nitro-9-nitroso carbazole, Koo, S. Encyclopedia of Reagents for Organic Synthesis, Paquette, L. A. Ed, Wiley, London, 1995, vol 6, pp 3747vvvv.

Highly Efficient Synthesis of Methyl-Substituted Conjugate Cyclohexenones, Byong-Don Chong.; Yong-Il Ji.;Seong-Soo Oh.; Jea-Deuk Yang.; Sangho Koo. J. Org. Chem, 1997, 62, 9323.

Diallylic Sulfides as Key Structures for Carotenoid Syntheses, Hojin Choi.; Minkoo Ji.; Minsoo Park, In-Kyun Yun.; Seong-Soo Oh.; Sangho Koo. J. Org. Chem, 1999, 64, 8051.

 Highly Efficient Synthesis of Bicyclo[3.3.1]nonane Skeleton, Jae-Deuk Yang.; Moon-Soo Kim.; Miai Lee.; Woonphil Baik.; Sangho Koo.; Synthesis, 2000, 6,  801-804.

A Highly Efficient Chain-Extension Process in the Systematic Syntheses of Carotenoid Natural Products, Minkoo Ji.; Hojin Choi.; Minsoo Park.; Minyong Kee.; Young Cheol Jeong.; Sangho Koo. Angew. Chem. Int. Ed. 2001, 40(19), 3627.

Selective Oxidation of Allylic Sulfindes by Hydrogen Peroxide with the Trirutile-type Solide Oxide Catalyst LiNbMoO6, Soojin Choi.; Jae-Deuk Yang.; Minkoo Ji.; Hojin Choi.; Minyong Kee.; Kwang-Hyun Ahn.; Song-Ho Byeon.; Woonphil Baik.; Sangho Koo. J. Org. Chem. 2001, 66(24), 8192.

Mn(III)-Mediated Radical Cyclization for 1-Octalone Synthesis, Miai Lee.; Jae-Deuk Yang.; Moon-Soo Kim.; Hye-Sun Jeon.; Woonphil Baik.; Sangho Koo. Bull. Korean Chem. Soc. 2002, 23(5), 736.

Allylic sulfones containing triene moieties a key synthons for carotenoid synthesis, Minkoo Ji.; Hojin Choi.; Youngcheol.; Jingquan Jin.; Woonphil Baik.; Sijoon Lee.; Jeongsoo Kim.; Minsoo Park.; Sangho Koo. Helvetica Chimica Acta. 2003, 86(7), 2620.

The Friedel-Crafts Alylation of a Preny Group Stabilized by a Sulfone Moiety: Expeditious Syntheses of Ubiquinones and Menaquinones, Jae-Hong Min.; Jun-Sup Lee.; Jae-Deuk Yang.; Sangho Koo. J. Org. Chem. 2003, 68(20), 7925.

The intramolecular Baylis Hillman reaction: easy preparation of versatile substrates, facile reactions, and synthetic applications, Jung Eun Yeo.; Xiuling Yang.; Hee Jin Kim.; Sangho Koo. Chem. Commun., 2004, 236.

Highly Efficient and General Syntehtic Method of Various Retinyl Ethers, Jun-Sup Lee.; Young-Cheol Jeong.; Minkoo J.; Woonphil Baik.; Sijoon Lee.; Sangho Koo. Synlett., 2004, 11, 1937.

Preparetion of the conjugated polyene chains with the 1,4-dimethyl substitution, Hye-Sun Jeon.; Sangho Koo.; Tetrahedron Letters, 2004, 45(38), 7023.

General and systematic synthetic entry to carotenoid natural products, Young Cheol Jeong.; Minkoo Ji.; Jun-sup Lee.; Jae-Deuk Yang.; Jingquan Jin.; Woonphil Baik.; Sangho Koo.Tetrahedron, 2004, 60(45), 10181.

Stereoselective and Convergent Syntheses of Retinoic Acid and Its Ester Derivatives by the Sulfone Olefination Reaction, Hye Sun Jeon.; Jung Eun Yeo.; Sangho Koo. Synthesis, 2004, 17, 2813.

Efficient Syntheses of the Keto-carotenoids Canthaxanthin, Astaxanthin, and Astacene, Seyoung Choi.; Sangho Koo. J. Org. Chem., 2005, 70(8), 3328.

Preparation of 1,4-hydrobenzoquinones by the PCC/SiO2-promoted double oxidation of 3-cyclohexene-1,2-diols, Hee jin Kim.; Sangho Koo.Org.Biomol.Chem., 2005, 3, 3479.

Sulfone Coupling and Double-Elimination Strategy for Carotenoid Synthesis, Samar Kumar Guha.; Sangho Koo. J. Org. Chem., 2005, 70, 9662.

TMS·OTf-Catalyzed -bromination of carbonyl compounds by N-bromosuccinimide,Samar Kumar Guha, Bo Wu, Beom Soo Kim, Woonphil Baik and Sangho Koo, Tetrahedron Letters.,47 (2006) 291. 

Origin of the Diastereoselection in the Indium-Mediated Addition of Haloallylic Sulfones to Aldehydes,Min, Jae-Hong; Jung, Se-Young; Wu, Bo; Oh, Jung Taek; Lah, Myoung Soo; Koo, Sangho, Organic Letters  (2006),  8(7),  1459-1462

Stereoselective Synthesis of Allylic Sulfones via the Oxonia-Cope Rearrangement of Homoallylic Alcohols Containing a Homoallylic Sulfone Moiety, Jung, Se-Young; Min, Jae-Hong; Oh, Jung Taek; Koo, Sangho,Journal of Organic Chemistry  (2006),  71(13),  4823-4828

Journal of Organic Chemistry 2008, 73, 1991-1994 (General Preparation and Controled Cyclization of Acyclic Terpenoids)

Advanced Synthesis & Catalysis 2008, 350, 365-369 (Expeditious and Practical Synthesis of  Lycopene)

Journal of Organic Chemistry 2009, 74, 917-920 (Ring-Expansion Protocol: Preparation of Synthetically Versatile Dihydrotropones)

Chemistry: A European Journal 2010, 16, 7395 - 7399 (Conductance Control in Stabilized Carotenoid Wires)

Pure and Applied Chemistry 2011, 83 , 3, 613 - 620 ( Convergent synthesis of new types of stabilized carotenoid compounds)

Physical Chemistry Chemical Physics 2011,13, 6340–6351 ( Ultrafast excited state dynamics and spectroscopy of 13,130-diphenyl-b-carotene)

Organic Letters 2011,13,10, 2682-2685 (Selective Deoxygenation of Allylic Alcohol: Stereocontrolled Synthesis of Lavandulol)

Europeon Journal of Organic chemistry ; 2012, 4954-4962 (Synthesis of Conzyme Q10)

Molecules ; 2012,17,12804-12811 (Bis-sulfonic acid Ionic Liquids for the Conversion of Fructose to 5-Hydroxymethyl-2-furfural)

Europeon Journal of Organic chemistry ; 2012, 6976-6985 (Mechanism and Scope of the Mn--initiated Oxidation of beta-Ketocarbonyl Compounds ; Furan Synthesis)

 

Chemistry: A European Journal  ; 2013, 19 10832-10835 (Combined Effect of Polar Substituents on the Electronic Flows in the Carotenoid Molecular Wire)

 

Journal of Organic Chemistry; 2014, 79(10), 4712-4717 (Sulfone-Mediated Syntheses of Crocetin Derivatives: Regioselectivity of Highly Functionalized Building Blocks)

   
   

Book

  1. Encyclopedia of Reagents for Organic Synthesis, Wiley, 1995: Allyl Trifluoromethanesulfonate Vol. 1, pp 130.

  2. Encyclopedia of Reagents for Organic Synthesis, Wiley, 1995: Bis(N-propylsalicylideneaminato)cobalt(II) Vol. 1, pp 552.

  3. Encyclopedia of Reagents for Organic Synthesis, Wiley, 1995: 3-Nitro-9-nitrosocarbazole Vol. 6, pp 3747.

  4. Encyclopedia of Reagents for Organic Synthesis, Wiley, 1995: N-Phenylcampholylhydroxamic Acid Vol. 6, pp 3965.

  5. Encyclopedia of Reagents for Organic Synthesis, Wiley, 1995: Thallium(I) Acetate Vol. 7, pp 4832.

     

Patent List

  1. Preparation method of substituted 2-cyclohexenones
    (a) Korean Patent Application,
    KR-1997-13534,1997.04.11., (b) Registration, 0194062, 1999.02.06.

  2. Compound comprising polyene chain structure and preparing method thereof
    (a) Korean Patent Application,
    KR-1998-47549, 1998.11.06,  (b) PCT Application, PCT/KR99/00648, 1999.10.28, Publication WO 00/27810, 2000.05.18. (c)US Patent Application, US 09/435,336, 1999.11.05. (d) Korean Patent Application, KR-2001-7003782, 2001.03.20. (e) Japanese Patent Application, JP-2000-580990, 2001.04.03. (f) Chinese Patent Application, CN-99812480.X, 2001.04.23 (g) European Patent Application (England, Germany, Switzerland, France), 99951244.5, 2001.05.03.

  3. Selective oxidation of sulfides by the use of an oxidant system consisting of LiNbMoO6 and H2O2
    (a) Korean Patent Application,
    KR-2000-09701, 2000.02.23. (b) Korean Patent Application, KR-2001-10165, 2001.02.21. (c) PCT Application, PCT/KR01/00252, 2001. 02. 22, Publication WO 01/62719, 2001.08.30.

  4. General synthetic entry to Carotenoid polyene chain compound
    (a) Korean Patent Application,
    KR-2000-10376, 2000.03.02.

  5. A Process for Preparing Carotenoid Polyene Chain Compounds and Intermediates for Preparing the Same
    (a)
    PCT Application, PCT/KR00/01375, 2000.11.29, Publication WO 01/64630, 2001.09.07.

  6. Synthesis of the Bicyclo[3.3.1]nonane structure
    (a) Korean Patent Application,
    KR-2000-16300, 2000.03.27.

  7. A highly efficient synthetic method of retinoic acid
    (a) Korean Patent Application,
    KR-2000-77567, 2000.12.01.

  8. Allylic sulfones containing conjugated polyene moieties, preparation method thereof, and a process for preparing
    lycopene by using the same compound as an intermediate
    (a) Korean Patent Application,
    KR-2001-01454, 2001.01.03.

  9. Practical Synthetic Method for Vitamin A
    (a) Korean Patent Application,
    KR-2001-19516, 2001.04.12.

  10. A Process for Making b-carotene
    (a) US Patent Registration,
    US 6,297,416, 2001.09,27.

  11. Diallylic Sulfides and Process for Making the Same
    (a) US Patent Application,
    US 09/873,672, 2001.06.04. (b) USPatent Registration,
    US 6,326,519, 2001.12.04.

  12. Process for Preparing 2,7-dimethyl-2,4,6-octatriene-1,8-dial
    (a) US Patent Application,
    US 09/965,059, 2001.09.27.

  13. A Highly Efficient Synthetic Method of 4-Chloro-3-methyl-2-butenyl Phenyl Sulfide and Di(4-chloro-3-methyl-2- butenyl) Sulfide as Key Compounds for Carotenoid Natural Product Syntheses
    (a) Korean Patent Application,
    KR-2001-67305, 2001.10.31.