Prof. Sangho Koo

 

¢ÂAffiliation:

Department of Chemistry

Department of Energy Science and Technology

Myongji University

Myongji-Ro 116, Cheoin-Gu, Yongin, Gyeonggi-Do, 17058, Korea

ph) +82-31-330-6185; Fax) +82-31-335-7248

E-mail) sangkoo@mju.ac.kr  Home) http://www.kooslab.org

¢ÂEducation
   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

¢ÂProfessional Career
 
  1994.03~present: : Professor in chemistry, Myonji UniversityProfessor in Chemistry, Myongji University
 
  2006.02~present:   Special Visiting Professor, Chemical Biotechnology, School of Pharmacy,                                 East China University of Science and Technology, Shanghai, China

   2006.03~2013.02:  Professor in Nano Science and Engineering, Myongji University

   2013.03~present:    Professor in Energy Science and Technology, Myongji University
 
  2017.02~2021.01:  Dean of Natural Science, Myongji University
   2019.01~present:    Associate Editor, Journal of the Korean Chemical Society
 
  2019.09~present:    Guest Professor, Institute of Traditional Chinese Medicine,

                                  Tianjin University of Traditional Chinese Medicine, Tianjin,China                      

  2020.01~present:      Reginal Chairman of Korean Chemical Society in Gyeonggi Province

 

¢ÂResearch Areas

1. Development of Efficient Cyclization Methods: Efficient synthetic methods for five-, six-, and seven-membered rings have been developed, and the syntheses of polycyclic structures using those compounds are under investigation. We are currently working on the Mn(III)-catalyzed oxidative hetero-aromatic cyclization for the syntheses of furan, pyrrole, indole, piperazinones.

2. Chemistry of Isoprenoid: Isoprenoid can be classified into terpenoid, carotenoid, and steroid. We have developed various bi-functionalized C5 prenyl building blocks that can be efficiently used in the chain-extension processes for making various isoprenoid natural products. We adopted the 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 using our C10 bis(chloroallylic) sulfide, or C10 dialdehyde, or even C20 diphosphonate. We extended this strategy to make other important carotenoid compounds. We further pursue the synthesis of terpenoid and steroid compounds by the combined use of our cyclization and chain-extension strategies. Followings are the carotenoid compounds that we have made so far: Vitamin A, Vitamin K, Tretinoin, Isotretinoin, Tocoretinoate, b-carotene, Lycopene, Lycophyll, Nor-Bixin, Crocetin, Zeaxanthin, Astaxanthin, Canthaxanthin, Coenzyme Q-10, and Abscisic acid.

3. Conducting Molecular Wires: Based on our methods of the carotenoid synthesis, we were able to construct the conjugated polyene chains with variable lengths. This conjugated polyene chains, which conduct electrons, can be stabilized by attaching phenyl substituents to the chain. We are preparing various organic conducting wires with different resistances. We are going to build up various molecular electronic circuits with diverse conductance

 4. Biomass conversion: Efficient conversion methods of sugars into useful platform chemicals such as 5-hydroxymethylfurfural (5-HMF) and 5-hydroxymethylpyrrole-2-carbaldehydes (pyrralines) are being investigated. A bis(sulfonic acid)-ionic liquid was utilized for fructose conversion to 5-HMF. The optimal condition using DMSO and oxalic acid transformed glucose and primary amines into pyrralines. This one-pot conversion of sugars into pyrralines is being applied to the total synthesis of biologically active natural products, (–)-Hanishin, Lobechine, and Magnolamide. Biomass conversion of ribose into sustainable platform chemicals as intermediates for new drug synthesis is underway


¢Â
Research Paper List (since 1995)

1.    ¡°General Synthetic Entry to Highly-Oxygenated Angularly-Fused Polycyclic Aromatic Compounds¡± S. Koo, L. S. Liebeskind,* J. Am. Chem. Soc. 1995, 117, 3389-3404.

2.    ¡°Microbial Deoxygenation of N-Oxides with Baker's Yeast-NaOH¡± W. Baik,* D. I. Kim, S. Koo, J. U. Rhee, S. H. Shin, B. H. Kim, Tetrahedron Lett. 1997, 38, 845-848.

3.    ¡°Highly Efficient Synthesis of Methyl-Substituted Conjugate Cyclohexenones¡± B.-D. Chong, Y.-I. Ji, S.-S. Oh, J.-D. Yang, W. P. Baik, S. Koo,* J. Org. Chem. 1997, 62, 9323-9325.

4.    ¡°Chemoselective Reactions of Anthrone with ¥á,¥â-Unsaturated Ketones¡± W. Baik,* C. H. Yoon, K. C. Lee, H. J. Lee, S. Koo, J. Kim, B. Yoon, H. Kim, J. Chem. Res. 1998, 358-359.

5.    ¡°LiAlH4 Promoted Reductive Deoxygenation of Hydroxybenzyl Alcohols via Benzoquinone Methide Intermediates¡± W. Baik,* H. J. Lee, S. Koo, B. H. Kim, Tetrahedron Lett. 1998, 39, 8125-8128.

6.    ¡°Photostimulated Reductive Cyclization of o-Nitrophenylazo Dyes Using Sodium Hydroxide in Isopropyl Alcohol. A New Synthesis of 2-Aryl-2H-benzotriazoles¡± W. Baik,* C. H. Yoo, S. Koo, H. Kim, Y. H. Hwang, B. H. Kim, S. W. Lee, Heterocycles 1999, 51, 1779-1783.

7.    ¡°Diallylic Sulfides as Key Structures for Carotenoid Syntheses¡± H. J. Choi, M. Ji, M. Park, I.-K. Yun, S.-S. Oh, W. Baik, S. Koo,* J. Org. Chem. 1999, 64, 8051-8053.

8.    ¡°NBS-Promoted Reactions of Symmetrically Hindered Methylphenols via p-Benzoquinone Methide¡± W. Baik,* H. J. Lee, J. M. Jang, S. Koo, B. H. Kim, J. Org. Chem. 2000, 65, 108-115.

9.    ¡°Highly Efficient Synthesis of Bicyclo[3.3.1]nonane Skeleton¡± J.-D. Yang, M.-S. Kim, M. Lee, W. Baik, S. Koo,* Synthesis 2000, 801-804.

10. ¡°Highly Efficient Chain-extension Process in the Systematic Syntheses of Carotenoid Natural Products¡± M. Ji, H. Choi, M. Park, M. Kee, Y. C. Jeong, S. Koo,* Angew. Chem., Int. Ed. 2001, 40, 3627-3629.

11.¡°Selective Oxidation of Allylic Sulfides by Hydrogen Peroxide with Trirutile-type Solid Oxide Catalyst - LiNbMoO6¡± S. Choi, J.-D. Yang, M. Ji, H. Choi, M. Kee, K.-H. Ahn, S.-H. Byeon, W. Baik, S. Koo,* J. Org. Chem. 2001, 66, 8192-8198.

12. ¡°The Reactivity and Stability Studies of Benzoquinone Methides by Ab Initio Calculations¡± W. Baik,* S. J. Kim, E.-Y. Hurh, S. Koo, B. H. Kim, Bull. Korean Chem. Soc. 2001, 22, 1127-1130.

13. ¡°Mn(III)-Mediated Radical Cyclization for ¡â1-3-Octalone Synthesis¡± M. Lee, J.-D. Yang, M.-S. Kim, H.-S. Jeon, W. Baik, S. Koo,* Bull. Korean Chem. Soc. 2002, 23, 736-740.

14. ¡°Identification of FM001 as Plant Growth-Promoting Substance from Acremonium strictum MJN1 Culture¡± J.-H. Jung, D.-M. Shin, W.-C. Bae, S.-K. Hong, J.-W. Suh, S. Koo, B.-C. Jeong,* J. Microbiol. Biotech. 2002, 12, 327-330.

15. ¡°Allylic Triene Sulfones as Key Synthons for Carotenoid Synthesis¡± M. Ji, H. Choi, Y. C. Jung, J. Jin, W. Baik, S. Lee, J. S. Kim, M. Park, S. Koo,* Helv. Chim. Acta 2003, 86, 2620-2628.

16. ¡°The Friedel-Crafts Allylation of a Prenyl Group Stabilized by a Sulfone Moiety - Expeditious Syntheses of Ubiquinones and Menaquinones¡±J.-H. Min, J.-S. Lee, J.-D. Yang, S. Koo,* J. Org. Chem. 2003, 68, 7925-7927.

17. ¡°The intramolecular Baylis-Hillman reaction: easy preparation of versatile substrates, facile reactions, and synthetic applications¡± J.-E. Yeo, X. Yang, H. J. Kim, S. Koo,* Chem. Commun. 2004, 236-237.

18. ¡°Highly Efficient and General Synthetic Method of Various Retinyl Ethers¡± J. S. Lee, Y. C. Jeong, M. Ji, W. Baik. S. Lee, S. Koo,* Synlett 2004, 1937-1940.

19. ¡°A computational Investigation of the Stability of Cyclopropyl Carbenes¡± W. Baik,* C. H. Yoon, S. Koo, B. H. Kim, Bull. Korean Chem. Soc. 2004, 25, 90-96.

20. ¡°Preparation of the conjugated polyene chains with the 1,4-dimethyl substitution¡± H.-S. Jeon, S. Koo,* Tetrahedron Lett. 2004, 45, 7023-7026.

21. ¡°Lewis acid-catalyzed reactions of anthrone: Preference for cycloaddition reaction over conjugate addition depending on the functionality of ¥á,¥â-unsaturated carbonyl compounds¡± W. Baik,* C. H. Yoon, S. Koo, H. Kim, J. Kim, J. Kim, S. Hong, Bull. Korean Chem. Soc. 2004, 25, 491-500.

22. ¡°General and systematic synthetic entry to carotenoid natural products¡± Y. C. Jeong, M. Ji, J. S. Lee, J.-D. Yang, J. Jin, W. Baik, S. Koo,* Tetrahedron 2004, 60, 10181-10185.

23. ¡°Stereoselective and Convergent Syntheses of Retinoic Acid and Its Ester Derivatives by the Sulfone Olefination Reaction¡± H.-S. Jeon, J. E. Yeo, Y. C. Jeong, S. Koo,* Synthesis 2004, 2813-2820.

24. ¡°Efficient Syntheses of Keto-carotenoid Canthaxanthin, Astaxanthin, and Astacene¡± S. Choi, S. Koo,* J. Org. Chem. 2005, 70, 3328-3331.

25. ¡°Efficient one-pot transformation of aminoarenes to haloarenes using halodimethylisulfonium halides generated in situ¡± W. Baik,* W. Luan, H. J. Lee, C. H. Yoon, S. Koo, B. H. Kim, Can. J. Chem. 2005, 83, 213-219.

26. ¡°Preparation of 1,4-hydrobenzoquinones by the PCC/SiO2-promoted double oxidation of 3-cyclohexene-1,2-diols¡± H. J. Kim, S. Koo,* Org. Biomol. Chem. 2005, 3, 3479-3481.

27. ¡°Sulfone Coupling and Double Elimination Strategy for Carotenoid Synthesis¡± S. K. Guha, S. Koo,* J. Org. Chem. 2005, 70, 9662-9665.

28. ¡°TMS·OTf-Catalyzed ¥á-bromination of carbonyl compounds by N-bromosuccinimide¡± S. K. Guha, B. Wu, B. S. Kim, W. Baik, S. Koo,* Tetrahedron Lett. 2006, 47, 291-293.

29. ¡°Origin of the Diastereoselection in the Indium-mediated Addition of Haloallylic Sulfones to Aldehydes¡± J.-H. Min, S.-Y. Jung, B. Wu, J. T. Oh, M. S. Lah, S. Koo,* Org. Lett. 2006, 8, 1459-1462.

30. ¡°Stereoselective Synthesis of Allylic Sulfones via the Oxonia-Cope Rearrangement of Homoallylic Alcohols Containing a Homoallylic Sulfone Moiety¡± S.-Y. Jung, J.-H. Min, J. T. Oh, S. Koo,* J. Org. Chem. 2006, 71, 4823-4828.

31. ¡°Expeditious and Practical Synthesis of Lycopene¡± E. Choi, J. E. Yeo, S. Koo,* Adv. Synth. Catal. 2008, 350, 365-369.

32. ¡°General Preparation and Controlled Cyclization of Acyclic Terpenoids¡± J. Kuk, B. S. Kim, H. Jung, S. Choi, J.-Y. Park, S. Koo,* J. Org. Chem. 2008, 73, 1991-1994.

33. ¡°Ring-Expansion Protocol: Preparation of Synthetically Versatile Dihydrotropones¡± Y.-S. Do, R. Sun, H. J. Kim, J. E. Yeo, S.-H. Bae, S. Koo,* J. Org. Chem. 2009, 74, 917-920.

34. ¡°Synthesis of highly conductive poly(3,4-ethylenedioxythiophene) fiber by simple chemical polymerization¡± W. Baik, W. Luan, R. H. Zhao, S. Koo, K.-S. Kim, Synth. Metals 2009, 159, 1244-1246.

35. ¡°Conductance Control in the Stabilized Carotenoid Wires¡± J. Maeng, S. B. Kim, N. J. Lee, E. Choi, S.-Y. Jung, I. Hong, S.-H. Bae, J. T. Oh, B. Lim, J. W. Kim, C. J. Kang, S. Koo,* Chem. Eur. J. 2010, 16, 7395-7399.

36. ¡°Convergent synthesis of new types of stabilized carotenoid compounds¡± S. B. Kim, H. Kim, B. Lim, J. Maeng, S.-H. Bae, E. Choi, J. T. Oh, I. Hong, S.-Y. Jung, J. E. Yeo, S. Koo,* Pure Appl. Chem. 2011, 83, 613-620.

37. ¡°Ultrafast excited state dynamics and spectroscopy of 13,13'-diphenyl-¥â-carotene¡± K. Golibrzuch, F. Ehlers, M. Scholz, R. Oswald, T. Lenzer, K. Oum,* H. Kwon, S. Koo,* Phys. Chem. Chem. Phys. 2011, 13, 6340-6351.

38. ¡°Selective Deoxygenation of Allylic Alcohol; Stereo-controlled Synthesis of Lavandulol¡± H. J. Kim, L. Su, H. Jung, S. Koo,* Org. Lett. 2011, 13, 2682-2685.

39. ¡°Mn(III)-Promoted Tandem Oxidation and Cyclization of ¥â-Ketoester Derivatives of Terpenoids¡± Z. Li, H. Jung, M. Park, M. Lah, S. Koo,* Adv. Synth. Catal. 2011, 353, 1913-1917.

40. ¡°Synthesis of Coenzyme Q-10¡± E.-T. Oh, H. J. Kim, J. T. Oh, L. Su, I. Yun, K. Nam, J.-H. Min, J. W. Kim, S. Koo,* Eur. J. Org. Chem. 2012, 4954-4962.

41. ¡°Bis-sulfonic Acid Ionic Liquids for the Conversion of Fructose to 5-Hydroxymethyl-2-furfural¡± S. E. Sim, S. Kwon, S. Koo,* Molecules 2012, 17, 12804-12811.

42. ¡°Mechanism and Scope of the Mn(III)-Initiated Oxidation of beta-Ketocarbonyl Compounds; the Furan Synthesis¡± C. Wang, Z. Li, Y. Ju, S. Koo,* Eur. J. Org. Chem. 2012, 6976-6985.

43. ¡°Combined Effect of Polar Substituents on the Electronic Flows in the Carotenoid Molecular Wires¡± Y. Zhao, S. Lindsay,* S. Jeon, H.-J. Kim, L. Su, B. Lim, S. Koo,* Chem. Eur. J. 2013, 19, 10832-10835.

44. ¡°Sulfone-Mediated Syntheses of Crocetin Derivatives: Regioselectivity of Highly Functionalized Building Blocks¡± E.-T. Oh, Y.-H. Kim, J. Jin, L. Su, J.-A. Seo, S. Koo,* J. Org. Chem. 2014, 79, 4712-4715.

45. ¡°Catalytic Oxidation of beta-Ketoester by Mn(III)/Co(II) and Consecutive Cyclization to Heterocycles¡± Y. Ju, D. Miao, J. G. Seo, S. Koo,* Adv. Synth. Catal. 2014, 356, 3059-3066.

46. ¡°Resonance Raman Spectra of Carotenoid Molecules: Influence of Methyl Substitutions¡± M. Macernis,* D. Galzerano, J. Sulskus, E. Kish, Y.-H. Kim, S. Koo, L. Valkunas, B. Robert, J. Phys. Chem. A 2015, 119, 56-66.

47. ¡°Regioselective Synthesis of 1,3- and 1,2-Tocopheryl Glyceride Ethers of Carboxylic Acids¡± B. S. Choi, J. Choi, S. Bak, S. Koo,* Eur. J. Org. Chem. 2015, 514-524.

48. ¡°Synthesis and characterization of multi-walled carbon nanotubes-supported dibenzo-14-crown ether with proton ionizable carboxyl sidearm as Li+ adsorbents¡± R. E. C. Torrejos, G. M. Nisola, M. J. Park, H. K. Shon, J. G. Seo, S. Koo, W.-J. Chung, Chem. Engineer. J. 2015, 264, 89-98.

49. ¡°Tandem Catalytic Oxidative Deacetylation of Acetoacetic Esters and Hetero Aromatic Cyclizations¡± Y. Ju, D. Miao, R. Yu, S. Koo,* Org. Biomol. Chem. 2015, 13, 2588-2599.

50. ¡°A Chain Extension Method for Apocarotenoids; Lycopene and Lycophyll Syntheses¡± J. Choi, E.-T. Oh, S. Koo,* Arch. Biochem. Biophys. 2015, 572, 142-150.

51. ¡°Enhanced biological activity of carotenoids stabilized by phenyl groups¡± J. S. You, S. Jeon, Y. J. Byun, S. Koo,* S. S. Choi,* Food Chem. 2015, 177, 339-345.

52. ¡°Esterification of carboxylic acids with alkyl halides using imidazolium based dicationic ionic liquids containing bis-?trifluoromethane sulfonimide anions at room temperature¡± A. H. Jadhav, K. Lee, S. Koo, J. G. Seo,* RSC Advances 2015, 5, 26197-26208.

53. ¡°Fine-tuning of single-molecule conductance by tweaking both electronic structure and conformation of side substituents¡± A. Aragones, N. Darwish, J.O. Im, B. Lim, J. Choi, S. Koo,* I. Diez-Perez,* Chem. Eur. J. 2015, 21, 7716-7720.

54. ¡°One-Pot Conversion of Carbohydrates into Pyrrole-2-Carbaldehydes as Sustainable Platform Chemicals¡± A. Nirmal Das, S. Kwon, W.-J. Chung, S. Koo,* J. Org. Chem. 2015, 80, 7693-7701.

55. ¡°Synthesis of Tribenzotropone by Ring Expansion of Phenanthren-9,10-dione¡± J. Choi, H. Jung, J. E. Yeo, S. Koo,* Synthesis 2015, 47, 2971-2975.

56. ¡°Liquid-liquid extraction of lithium using lipophilic dibenzo-14-crown-4 ether carboxylic acid in hydrophobic room temperature ionic liquid¡± R. E. C. Torrejos, G. M. Nisola, H. S. Song, J. W. Han, C. P. Lawagon, J. S. Seo, S. Koo, H. Kim, W.-J. Chung, Hydrometallurgy 2016, 164, 362-371.

57. ¡°Efficient preparation method of 4-hydroxybenzoic esters – Oxidation of substituted Hagemman¡¯s ester¡± S. Kang, D. Kim, I. J. In, S. Koo* Tetrahedron Lett. 2017, 58, 2264-2266.

58. ¡°Design of lithium selective crown ethers: Synthesis, extraction and theoretical binding studies¡± R. E. C. Torrejos, G. M. Nisola, H. S. Song, L. A. Limjuco, C. P. Lawagon, K. J. Parohinog, S. Koo, J. W. Han, W.-J. Chung, Chem. Engineer. J. 2017, 326, 921-933.

59. ¡°Aethusifolins A–D: Four new components from a traditional Mongolian medicinal herb Clematis aethusifolia Turcz¡± Y. Chang, P. Zhang, J. Jurhiin, X. Zhang, W. Borgihiin, H. Zhao, S. Koo, W.-D. Rausch, B. Agula, B. Bao, Phytochem. Lett. 2017, 22, 87-91.

60. ¡°Systematic synthesis of diphenyl-substituted carotenoids as molecular wires¡± B. Lim, E.-T. Oh, J.O. Im, K. S. Lee, H. Jung, M. Kim, D. Kim, J. T. Oh, S.-H. Bae, W.-J. Chung, K.-H. Ahn, S. Koo* Eur. J. Org. Chem. 2017, 6390-6400.

61. ¡°Aerosol Cross-Linked Crown Ether Diols Melded with Poly(vinyl alcohol) as Specialized Microfibrous Li+ Adsorbents¡± L. A. Limjuco, G. M. Nisola, R. E. C. Torrejos, J. W. Han, H. S. Song, K. J. Parohinog, S. Koo, S.-P. Lee, W.-J. Chung, ACS Appl. Mater. Interfaces 2017, 9, 42862-42874.

62. ¡°Deprotection of durable benzenesulfonyl protection for phenols – efficient synthesis of polyphenols¡± M. S. Alam, S. Koo* Synth. Commun. 2018 , 48, 247-254.

63. ¡°Role of Ring Ortho Substituents on the Configuration of Carotenoid Polyene Chains¡± M. Kim, H. Jung, A. C. Aragones, I. Diez-Perez, K.-H. Ahn, W.-J. Chung, D. Kim, S. Koo* Org. Lett. 2018, 20, 493-496.

64. ¡°Lycorin Displays Potent Antitumor Efficacy in Colon Carcinoma by Targeting STAT3¡± S. Wu, Y. Qiu, Y. Shao, S. Yin, R. Wang, X. Pang, J. Ma, C. Zhang, B. Wu, S. Koo, L. Han, Y. Zhang, X. Gao, T. Wang, H. Yu,* frontiers in Pharmacology, 2018, 9, 881/1-881/11.

65. ¡°Fast Assembly and High-Throughput Screening of Structure and Antioxidant Relationship of Carotenoids¡± D. Kim, G. Shi, Y. Kim, S. Koo* Org. Lett. 2019, 21, 714-718.

66. ¡°Aqueous Synthesis of 14-15-Membered Crown Ethers with Mixed O, N, and S Heteroatoms: Experimental and Theoretical Binding Studies with Platinum-Group Metals¡± R. E. C. Torrejos, G. M. Nisola, S. H. Min, J. W. Han, S. Koo, K. J. Parohinog, S. Lee, H. Kim, W.-J. Chung,* ChemPlusChem 2019, 84, 210-221.

67. ¡°7-?Deoxynarciclasine shows promising antitumor efficacy by targeting Akt against hepatocellular carcinoma¡± S. Yin,* Y. Qiu,* C. Jin,* R. Wang, S. Wu, H. Liu, S. Koo, L. Han, Y. Zhang, X. Gao, X. Pang, T. Wang and H. Yu International Journal of Cancer 2019, DOI:10.1002/ijc.32395.

68. ¡°Synthesis of Phenyl-2,2?-bichalcophenes and Their Aza-analogues by Catalytic Oxidative Deacetylation¡± X. Jiang, H. Jin, T. Wang, H. Yoo, S. Koo* Synthesis 2019, 51(17), 3259-3268. DOI:10.1055/s-0037-1611564.

69. ¡°Bromoacetate Olefination Protocol for Norbixin and Julia-Kocienski Olefination for Its Ester Syntheses¡± D. Kim, M. Alam, W.-J. Chung, S. Koo* ACS Omega 2019, 4(6), 10019-10024 (2019.06.07.).

70. ¡°Synthesis and application of novel hydroxylated thia-crown ethers as composite ionophores for selective recovery of Ag+ from aqueous sources¡± H. T. Fissaha, G. M. Nisola, F. K. Burnea, J. Y. Lee, S. Koo, S.-P. Lee, H. Kim, W.-J. Chung* Journal of Industrial and Engineering Chemistry 2020, 81, 415-426 (2020.01.25.).

71. ¡°Synthetic strategy for tetraphenyl-substituted all-E-carotenoids with improved molecular properties¡± B. Lim, H. Jung, H. Yoo, M. Park, H. Yang, W.-J. Chung, S. Koo* European Journal of Organic Chemistry 2020, (11), 1769-1777 (2020.03.16.).

72. ¡°Crown ethers "clicked" on fibrous polyglycidyl methacrylate for selective Li+ retrieval from aqueous sources¡± G. M. Nisola, K. J. Parohinoga, R. E. C. Torrejos, S. Koo, S.-P. Lee,* H. Kim,* W.-J. Chung,* Colloids and Surfaces A 2020, 595, 124709 (2020.04).

73. ¡°Concise and practical synthesis of (+)-Abscisic acid¡± D. Kim and S. Koo* ACS Omega 2020, 5(22), 13296-13302. (2020.05).

74. ¡°Syntheses of Chalcone-Derived Heteroaromatics with Anti-bacterial Activities¡± H. Jin, X. Jiang, H. Yoo, T. Wang, C.l G. Sung, U. Choi, C.-R. Lee,* H. Yu, S. Koo* ChemistrySelect 2020, 5(40), 12421-12424. (online Oct. 29, 2020).

75. ¡°Tuning Single-Molecule Conductance by Controlled Electric Field-Induced trans-to-cis Isomerisation¡± C.S. Quintans, D. Andrienko, K.F. Domke, D. Aravena, S. Koo, I. Díez-Pérez, A.C. Aragonès, Applied Sciences 2021, 11(8), 3317. (online Apr. 7, 2021).

¡°Multidentate thia-crown ethers as hyper-crosslinked macroporous adsorbent resins for the efficient Pd/Pt recovery and separation from highly acidic spent automotive catalyst leachate¡± R. E. C. Torrejos, E. C. Escobar, J. W. Han, S. H. Min, H. Yook, K. J. Parohinog, S. Koo, H. Kim, G. M. Nisola, W.-J. Chung, Chemical Engineering Journal 2021, 424, 130379.

¢ÂBook

1. Encyclopedia of Reagents for Organic Synthesis, Wiley, 1995: Allyl Trifluoromethanesulfonate Vol. 1, pp 130; Bis(N-propylsalicylideneaminato)cobalt(II)     Vol. 1, pp 552; 3-Nitro-9-nitrosocarbazole Vol. 6, pp 3747; N-Phenylcampholylhydroxamic Acid Vol. 6, pp 3965; Thallium(I) Acetate Vol. 7, pp 4832.

2. Science of Synthesis, Thieme, 2009: Vol. 45.30 Conjugated Polyenes.

3. e- Encyclopedia of Reagents for Organic Synthesis, Wiley, 2011: 4-Bromo-1-chloro-2-methyl-2-butene.

¢ÂPatent List (34 Korean patents and 16 International patents registration)

1.        ¡°Preparation method of substituted 2-cyclohexenones¡±(a) Korean Patent Application, KR 1997-13534, 1997.04.11. (b) Korean Patent Registration, KR 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), EP 99951244.5, 2001.05.03. (h) ¡°A Process for Making b-carotene¡± US Patent Registration, US 6,297,416, 2001.09,27. ¡°Diallylic Sulfides and Process for Making the Same¡± (i) US Patent Application (1st Divisional), US 09/873,672, 2001.06.04. (j) US Patent Registration, US 6,326,519, 2001.12.04. ¡°Process for Preparing 2,7-dimethyl-2,4,6-octatriene-1,8-dial¡± (k) US Patent Application (2nd Divisional), US 09/965,059, 2001.09.27. (l) US Patent Registration, US 6,403,838, 2002.06.11. (m) Korean Patent Registration, KR 0400262, 2003.09.20 (n) European Patent Registration, EP 1124800, 2004.01.07 (England, France, Germany, Switzerland).

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. (d) Korean Patent Registration, KR 0422437, 2004.03.02.

4.        ¡°General synthetic entry to Carotenoid polyene chain compound¡± (a) Korean Patent Application, KR-2000-10376, 2000.03.02. ¡°A Process for Preparing Carotenoid Polyene Chain Compounds and Intermediates for Preparing the Same¡± (b) PCT Application, PCT/KR00/01375, 2000.11.29, Publication WO 01/64630, 2001.09.07. (c) US patent Application, US 10/220,697, 2002.08.30. (d) Japanese Patent Application, JP 2001-563473, 2002.09.02. (e) European Patent Application, EP 00983496.1, 2002.09.30. (f) Chinese Patent Application, CN 00819443.2, 2002.10.18. (g) Korean Patent Registration, KR 0365696, 2002.12.09. (h) ¡°Carbon chain extending method of allylic sulfide¡± Korean Patent Application (Divisional), KR 2002-47507, 2002.08.12. (i) Korean Patent Registration, KR 0398652, 2003.09.03. (j) US patent registration, US 6,747,166, 2004.06.08. (k) Japanese Patent Registration, JP 3975434, 2007.06.29. (l) European Patent Registration, EP 1283826, 2008.03.26.

5.        ¡°Synthesis of the Bicyclo[3.3.1]nonane structure¡± (a) Korean Patent Application, KR 2000-16300, 2000.03.27. (b) Korean Patent Registration, KR 0365526, 2002.12.07.

6.        ¡°A highly efficient synthetic method of retinoic acid¡± (a) Korean Patent Application, KR 2000-77567, 2000.12.01. ¡°Practical and Efficient Synthetic Method of Retinoic Acid and Its Derivatives¡± (b) Korean Patent Application, KR 2001-74530, 2001.11.28. ¡°Process for the preparation of retinoic acid compounds and the intermediates required¡± (c) PCT Application, PCT/KR01/02078, 2001.12.01, Publication WO 02/44140, 2002.06.06 (d) Korean Patent Registration, KR 0424735, 2004.03.16.

7.        ¡°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. (b) Korean Patent Registration, KR 0400261, 2003.09.20.

8.        ¡°Practical Synthetic Method for Vitamin A¡± (a) Korean Patent Application, KR 2001-19516, 2001.04.12. ¡°Practical Synthetic Method of Retinoid and Carotenoid Compounds¡± (b) Korean Patent Application, KR 2002-19371, 2002.04.10. ¡°Process for the preparation of retinoid and carotenoid compounds from a common C-15 disulfone compound¡± (c) PCT Application, PCT/KR02/00660, 2002.04.11, Publication WO 02/92560, 2002.11.21. (d) Korean Patent Registration, KR 0477899, 2005.03.10.

9.        ¡°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. (b) Korean Patent Application, KR-2002-0066588, 2002.10.30. (c) PCT Application, PCT/KR02/02025, 2002.10.30. (d) US patent application, US 10/493,712, 2004.04.23. (e) Japanese Patent Application, JP 2004-540137, 2004.04.28. (f) Chinese Patent Application, CN 02821785.3, 2004.04.30. (g) European Patent Application, EP 02788903.9, 2004.05.24. (h) Korean Patent Registration, KR 0516743, 2005.09.09. (i) Korean Patent Registration (divisional), KR 0536342, 2005.12.06. (j) Japanese Patent Registration, JP 4265773, 2009.02.27. (k) Japanese Patent Registration, JP 4903774, 2012.01.13.

10.    ¡°Practical Synthetic Method of Teprenone¡± (a) Korean Patent Application, KR 2002-8831, 2002.02.19. (b) Korean Patent Registration, KR 0524257, 2005.10.20.

11.    ¡°Synthetic method of the para-hydroquinone compound containing allylic sulfone moiety that can be efficiently utilized for the preparation of coenzyme Q and vitamin K¡± (a) Korean Patent Application, KR 2003-50157, 2003.07.22. (b) Korean Patent Registration, KR 0514494, 2005.09.06.

12.    ¡°Preparation method of b-carotene¡± (a) Korean Patent Application, KR 2003-93819, 2003.12.19. (b) Korean Patent Registration, KR 1081115, 2011.11.01.

13.    ¡°An Efficient Preparation Method of Retinol Derivatives and Novel Retinyl Ether Compounds¡± (a) Korean Patent Application, KR 2003-94447, 2003.12.22. (b) Korean Patent Registration, KR 0569701, 2006.04.04.

14.    ¡°Preparing method of canthaxanthin¡± (a) Korean Patent Application, KR 2003-0095646, 2003.12.23. (b) Korean Patent Registration, KR 1019787, 2011.02.25.

15.    ¡°Stereoselective synthetic method of 13-cis-retinoic acid and all-trans-retinoic acid¡± (a) Korean Patent Application, KR 2003-0098676, 2003.12.29. (b) Korean Patent Registration, KR 0562771, 2006.03.14.

16.    ¡°Carotenoid intermediate compound, preparing method thereof, and method for preparing carotenoid compound, astaxanthin and astacene using the same¡± (a) Korean Patent Application, KR 2004-0000328, 2004.01.05. (b) Korean Patent Registration, KR 1088266, 2011.11.23.

17.    ¡°An efficient synthetic method of b-carotene¡± (a) Korean Patent Application, KR 2004-78975, 2004.10.05. (b) ¡°C10 Dialdehyde, Synthetic Method Thereof, and Synthetic Method of beta-Carotene Using the Same, PCT/KR2005/002273, 2005.07.15. (c) Korean Patent Registration, KR 0634884, 2006.10.10. (d) US Patent Application, US 11/576,580, 2007.04.03. (e) US Patent Registration, US 7,470,822, 2008.12.30.

18.    ¡°Stereoselective preparation method of allylic sulfones for carotenoid synthesis¡± (a) Korean Patent Application, KR 2006-0016458, 2006.02.20. (b) Korean Patent Registration, KR 0730987, 2007.06.15.

19.    ¡°Dialdehyde compound, preparation method thereof, and synthetic method of carotenoids using the same¡± (a) Korean Patent Application, KR 2006-0050248, 2006.06.05. (b) Korean Patent Registration, KR 0733023, 2007.06.21. (c) US Patent Application, US 12/308,028, 2008.12.05. (d) US Patent Registration, US 7,928,266, 2011.04.19. (e) US Patent Application, US 12/308,028, (divisional 1: 13/047,473; divisional 2: 13/047,524; divisional 3: 13/047,535) 2011.03.14. (f) US Patent Registration, US 8,158,838, 2012.04.17. (g) US Patent Registration, US 8,288,605, 2012.10.16.

20.    ¡°Useful intermediates for preparation of coenzyme Q-10, preparation method thereof, and preparation method of coenzyme Q-10 using them¡± (a) Korean Patent Application, KR 2006-0058348, 2006.06.27. (b) Korean Patent Registration, KR 0683231, 2007.02.08.

21.    ¡°Stable carotenoid molecular wires with variable resistance, and preparation method thereof¡± (a) Korean Patent Application, KR 10-2009-0058120, 2009.06.29. (b) Korean Patent Registration, KR 1179280, 2012.08.28.

22.    ¡°New functional glycerol derivatives of vitamin E and retinoic acid, and synthetic method of the same¡± (a) Korean Patent Application, KR 10-2011-0062209, 2011.06.27. (b) Korean Patent Registration, KR 1261270, 2013.04.30.

23.    ¡°Method for preparing carotenoid nanoparticle¡± (a) Korean Patent Application, KR 10-2013-0062777, 2013.05.31. (b) Korean Patent Registration, KR 1468308, 2014.11.26.

24.     ¡°C5 Sulfone Compound, Method for Preparing the Same, Method for Preparing Crocetin Dinitrile Using the Same, and Use Thereof¡± (a) Korean Patent Application, KR 10-2014-0039906, 2014.04.03. (b) Korean Patent Registration, KR 1574719, 2015.11.30.

25.    ¡°C5 Benzothiazolyl Sulfone Compound, Method for Preparing the Same, Method for Preparing Apocarotene Dialdehyde Compounds Using the Same, and Its Application to Lycopene Synthesis¡± (a) Korean Patent Application, KR 10-2014-0080647, 2014.06.30. (b) US Patent Application, US 14/751,294, 2015.06.26. (c) Korean Patent Registration, KR 1566159, 2015.10.30. (d) US Patent Registration, US 9,365,561, 2016.06.14.

26.    ¡°Synthesis of furan, thiophene, and pyrroles from acetoacetic esters¡±(a) Korean Patent Application, KR 10-2014-0111856, 2014.08.26. (b) Korean Patent Registration, KR 1623810, 2016.05.18.

27.    ¡°Synthesis of indoles from acetoacetic esters¡± (a) Korean Patent Application, KR 10-2014-0116313, 2014.09.02. (b) Korean Patent Registration, KR 1599969, 2016.02.26.

28.    ¡°Method for preparing pyrrole-2-carbaldehydes and pyrrolo-lactone using sugars¡± (a) Korean Patent Application, KR 10-2014-0127916, 2014.09.24. (b) Korean Patent Registration, KR 1675938, 2016.11.08.

29.    ¡°2,7-Diphenylocta-2,4,6-trienedial, method for preparing the same and method for preparing carotenoids containing phenyl substituents using the same¡± (a) Korean Patent Application, KR 10-2017-0082060, 2017.06.28. (b) Korean Patent Registration, KR 1937960, 2019.01.07.

30.    ¡°Novel pyrrolo-lactone and pyrrole compounds inducing cellular glutathione recovery effect against reactive oxygen species, and method for preparing the same¡± (a) Korean Patent Application, KR 10-2017-0121193, 2017.09.20. (b) Korean Patent Registration, KR 1951752, 2019.02.19.

31.    ¡°C20 Polyene bis(phosphonate) and method for synthesizing carotenoids using the same¡± (a) Korean Patent Application, KR 10-2018-0010221, 2018.01.26. (b) PCT Application, PCT/KR2019/000964, 2019.01.23 (c) Korean Patent Registration, KR 10-2092655, 2020.03.18.

32.    ¡°Bi-heteroaromatic compounds including bifuran, bithiophene, bipyrrole, and method for preparing the same¡± (a) Korean Patent Application, KR 10-2018-0099354, 2018.08.24. (b) Korean Patent Application with Priority claimed, KR 10-2019-0055375, 2019.05.13.

33.    ¡°Novel intermediates for preparing Norbixin or Bixin ethyl ester and method thereof¡± (a) Korean Patent Application, KR 10-2019-0020099, 2019.02.20. (b) Chinese Patent Application, CN 201910615006.2, 2019-07-09. (c) US Patent Application, US 16/510,243, 2019.07.12. (d) Korean Patent Registration, KR 10-2133791, 2020.07.08. (e) US Patent Registration, US 10,800,735, 2020.10.13.

34.    ¡°Pyrraline compounds, method for preparing the pyrraline compoumds, pierazin-2-one compounds and method for preparing the piperazine-2-one compounds¡± (a) Korean Patent Application, KR-10-2021-0011404, 2021.01.27.

35.    ¡°Novel Glyceride Compound and Preparation Method Thereof¡± (a) Korean Patent Application, KR-10-2021-0074037, 2021.06.08.

(updated by June 2021)

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