¢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.
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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.
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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
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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
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¢ÂResearch 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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