메뉴 건너뛰기




Volumn 1, Issue 5, 2009, Pages 897-908

Concise asymmetric synthesis of configurationally stable 4-trifluoromethyl thalidomide

Author keywords

[No Author keywords available]

Indexed keywords

3 TRIFLUOROMETHYL ACRYLIC ACID; 3 TRIFLUOROMETHYL PYROGLUTAMIC ACID; 4 TRIFLUOROMETHYL THALIDOMIDE; ACRYLIC ACID DERIVATIVE; GLUTAMIC ACID DERIVATIVE; THALIDOMIDE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 77953372156     PISSN: 17568919     EISSN: None     Source Type: Journal    
DOI: 10.4155/fmc.09.63     Document Type: Article
Times cited : (17)

References (80)
  • 1
    • 0025042316 scopus 로고
    • Synthesis, central nervous system activity and teratogenicity of a homothalidomide Arzneim
    • Eger K, Jalalian B, Verspohl EJ, Lupke NP. Synthesis, central nervous system activity and teratogenicity of a homothalidomide Arzneim. Forsch. 40, 1073-1075 (1990).
    • (1990) Forsch , vol.40 , pp. 1073-1075
    • Eger, K.1    Jalalian, B.2    Verspohl, E.J.3    Lupke, N.P.4
  • 2
    • 0016429845 scopus 로고
    • Tumor angiogenesis: A possible control point in tumor growth
    • Folkman J. Tumor angiogenesis: a possible control point in tumor growth. Ann. Intern. Med. 82, 96-100 (1975).
    • (1975) Ann. Intern. Med , vol.82 , pp. 96-100
    • Folkman, J.1
  • 3
    • 0026080801 scopus 로고
    • Thalidomide selectively inhibits tumor necrosis factor αproduction by stimulated human monocytes
    • Sampio EP, Sarno EN, Galilly R, Cohn ZA, Kaplan G. Thalidomide selectively inhibits tumor necrosis factor αproduction by stimulated human monocytes J. Exp. Med. 173, 699-703 (1991).
    • (1991) J. Exp. Med. , vol.173 , pp. 699-703
    • Sampio, E.P.1    Sarno, E.N.2    Galilly, R.3    Cohn, Z.A.4    Kaplan, G.5
  • 4
    • 0027230553 scopus 로고
    • Thalidomide exerts its inhibitory action on tumor necrosis factor αby enhancing mRNA degradation
    • Moreira, AL, Sampio EP, Zmuidzinas A, Frindt P, Smith KA, Kaplan G. Thalidomide exerts its inhibitory action on tumor necrosis factor αby enhancing mRNA degradation J. Exp. Med. 177, 1675-1680 (1993).
    • (1993) J. Exp. Med. , vol.177 , pp. 1675-1680
    • Moreira, A.L.1    Sampio, E.P.2    Zmuidzinas, A.3    Frindt, P.4    Smith, K.A.5    Kaplan, G.6
  • 5
    • 55249087667 scopus 로고    scopus 로고
    • Role of thalidomide in previously untreated patients with multiple myeloma
    • Musto P, D'Auria F, Pietrantuono G et al. Role of thalidomide in previously untreated patients with multiple myeloma. Expert Rev. Anticancer Ther. 8, 1569-1580 (2008).
    • (2008) Expert Rev. Anticancer Ther , vol.8 , pp. 1569-1580
    • Musto, P.1    D'Auria, F.2    Pietrantuono, G.3
  • 6
    • 53549098210 scopus 로고    scopus 로고
    • Thalidomide as a multitemplate for development of biologically active compounds
    • Hashimoto Y. Thalidomide as a multitemplate for development of biologically active compounds. Arch. Pharm. Chem. Life Sci. 341, 536-547 (2008).
    • (2008) Arch. Pharm. Chem. Life Sci , vol.341 , pp. 536-547
    • Hashimoto, Y.1
  • 7
    • 43249097561 scopus 로고    scopus 로고
    • Thalidomide for treatment of multiple myeloma: 10 years later
    • Palumbo A, Facon T, Sonneveld P et al. Thalidomide for treatment of multiple myeloma: 10 years later. Blood 111, 3968-3977 (2008).
    • (2008) Blood , vol.111 , pp. 3968-3977
    • Palumbo, A.1    Facon, T.2    Sonneveld, P.3
  • 8
    • 38449111448 scopus 로고    scopus 로고
    • The role of thalidomide in the management of erythema nodosum leprosum
    • Walker SL, Waters MF, Lockwood DN. The role of thalidomide in the management of erythema nodosum leprosum. Lepr. Rev. 78, 197-215 (2007).
    • (2007) Lepr. Rev. , vol.78 , pp. 197-215
    • Walker, S.L.1    Waters, M.F.2    Lockwood, D.N.3
  • 9
    • 2442621619 scopus 로고    scopus 로고
    • Discovery and development of bevacizumab, an anti-VEGF antibody for treating cancer
    • Ferrara N, Hillan KJ, Gerber HP, Novotny W. Discovery and development of bevacizumab, an anti-VEGF antibody for treating cancer. Nat. Rev. Drug Discov. 3, 391-400 (2004).
    • (2004) Nat. Rev. Drug Discov. , vol.3 , pp. 391-400
    • Ferrara, N.1    Hillan, K.J.2    Gerber, H.P.3    Novotny, W.4
  • 10
    • 27744566793 scopus 로고    scopus 로고
    • Thalidomide and dexamethasone: Therapy for multiple myeloma
    • Kumar S, Rajkumar SV. Thalidomide and dexamethasone: therapy for multiple myeloma. Expert Rev. Anticancer Ther. 5 759-766 (2005).
    • (2005) Expert Rev. Anticancer Ther , vol.5 , pp. 759-766
    • Kumar, S.1    Rajkumar, S.V.2
  • 11
    • 20444491613 scopus 로고    scopus 로고
    • Drug insight: Thalidomide as a treatment for multiple myeloma
    • Kumar S, Anderson KC. Drug insight: thalidomide as a treatment for multiple myeloma. Nat. Clin. Pract. Oncol. 2, 262-270 (2005).
    • (2005) Nat. Clin. Pract. Oncol. , vol.2 , pp. 262-270
    • Kumar, S.1    Anderson, K.C.2
  • 12
    • 0030882762 scopus 로고    scopus 로고
    • Taming TNF: Strategies to restrain this proinflammatory cytokine
    • Eigler A, Sinha B, Hartmann G, Endres S. Taming TNF: strategies to restrain this proinflammatory cytokine. Immunology Today 18, 487-492 (1997).
    • (1997) Immunology Today , vol.18 , pp. 487-492
    • Eigler, A.1    Sinha, B.2    Hartmann, G.3    Endres, S.4
  • 15
    • 1942534043 scopus 로고    scopus 로고
    • The evolution of thalidomide and its IMiD derivatives as anticancer agents
    • Bartlett JB, Dredge K, Dalgleish AG. The evolution of thalidomide and its IMiD derivatives as anticancer agents. Nat. Rev. Cancer 4, 314-322 (2004).
    • (2004) Nat. Rev. Cancer. , vol.4 , pp. 314-322
    • Bartlett, J.B.1    Dredge, K.2    Dalgleish, A.G.3
  • 16
    • 0035033777 scopus 로고    scopus 로고
    • Thalidomide in cancer: Potential uses and limitations
    • Singhal S, Mehta J. Thalidomide in cancer: potential uses and limitations. BioDrugs 15, 163-172 (2001).
    • (2001) BioDrugs , vol.15 , pp. 163-172
    • Singhal, S.1    Mehta, J.2
  • 17
    • 84883833410 scopus 로고
    • Thalidomide in the treatment of lepra reactions
    • Sheskin J. Thalidomide in the treatment of lepra reactions. Clin. Pharmacol. Ther. 6, 303-306 (1965).
    • (1965) Clin. Pharmacol. Ther , vol.6 , pp. 303-306
    • Sheskin, J.1
  • 18
    • 0018620980 scopus 로고
    • Chromatographic racemic separation of thalidomide and teratogenic activity of its enantiomers
    • Blaschke G, Klaft HP, Fickentscher K, Koehler F. Chromatographic racemic separation of thalidomide and teratogenic activity of its enantiomers. Arzneim. Forsch. 29, 1640-1642 (1979).
    • (1979) Arzneim. Forsch , vol.29 , pp. 1640-1642
    • Blaschke, G.1    Klaft, H.P.2    Fickentscher, K.3    Koehler, F.4
  • 19
    • 2542509655 scopus 로고    scopus 로고
    • A double-blind study of the sedative effects of the thalidomide enantiomers in humans
    • Hoglund P, Eriksson T, Bjorkman S. A double-blind study of the sedative effects of the thalidomide enantiomers in humans. J. Pharmacokinet. Biopharm. 26, 363-383 (1998).
    • (1998) J. Pharmacokinet. Biopharm. , vol.26 , pp. 363-383
    • Hoglund, P.1    Eriksson, T.2    Bjorkman, S.3
  • 20
    • 0028916174 scopus 로고
    • Stereospecific determination, chiral inversion in vitro and pharmacokinetics in humans of the enantiomers of thalidomide
    • Eriksson T, Bjorkman S, Roth B, Fyge A, Hoglund P. Stereospecific determination, chiral inversion in vitro and pharmacokinetics in humans of the enantiomers of thalidomide. Chirality 7, 44-52 (1995).
    • (1995) Chirality , vol.7 , pp. 44-52
    • Eriksson, T.1    Bjorkman, S.2    Roth, B.3    Fyge, A.4    Hoglund, P.5
  • 21
    • 0027114792 scopus 로고
    • Thalidomide enantiomers
    • Wintersk W, Frankus E. Thalidomide enantiomers. Lancet 339, 365 (1992).
    • (1992) Lancet , vol.339 , pp. 365
    • Wintersk, W.1    Frankus, E.2
  • 23
    • 0029990823 scopus 로고    scopus 로고
    • Enantioselective inhibition of TNF-αrelease by thalidomide and thalidomide-analogs
    • Wnendt S, Finkam M, Winter W, Ossing J, Rabbe G, Zwingenberger K. Enantioselective inhibition of TNF-αrelease by thalidomide and thalidomide-analogs. Chirality 8, 390-396 (1996).
    • (1996) Chirality , vol.8 , pp. 390-396
    • Wnendt, S.1    Finkam, M.2    Winter, W.3    Ossing, J.4    Rabbe, G.5    Zwingenberger, K.6
  • 24
    • 0028220747 scopus 로고
    • Investigations on the in vitro racemization of thalidomide by high-performance liquid chromatography
    • Knoche B, Blaschke G. Investigations on the in vitro racemization of thalidomide by high-performance liquid chromatography. J. Chromatogr. 2, 235-240 (1994).
    • (1994) J. Chromatogr. , vol.2 , pp. 235-240
    • Knoche, B.1    Blaschke, G.2
  • 25
    • 0842327350 scopus 로고    scopus 로고
    • Effect of 3-fluorothalidomide and 3-methylthalidomide enantiomers on tumor necrosis factor production and antitumor responses to the antivascular agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA)
    • Chung F, Palmer BD, Muller GW et al. Effect of 3-fluorothalidomide and 3-methylthalidomide enantiomers on tumor necrosis factor production and antitumor responses to the antivascular agent 5,6-dimethylxanthenone-4-acetic acid (DMXAA). Oncol. Res. 14, 75-82 (2003).
    • (2003) Oncol. Res. , vol.14 , pp. 75-82
    • Chung, F.1    Palmer, B.D.2    Muller, G.W.3
  • 26
    • 0031873804 scopus 로고    scopus 로고
    • Tumor necrosis factor-αproduction enhancing activity of substituted 3́-methylthalidomide: Influence of substituents at the phthaloyl moiety on the activity and stereoselectivity
    • Miyachi H, Kolso Y, Shirai R, Niwayama S, Liu JO, Hashimoto Y. Tumor necrosis factor-αproduction enhancing activity of substituted 3́-methylthalidomide: influence of substituents at the phthaloyl moiety on the activity and stereoselectivity. Chem. Pharm. Bull. 46, 1165-1168 (1998).
    • (1998) Chem. Pharm. Bull. , vol.46 , pp. 1165-1168
    • Miyachi, H.1    Kolso, Y.2    Shirai, R.3    Niwayama, S.4    Liu, J.O.5    Hashimoto, Y.6
  • 27
    • 0025137676 scopus 로고
    • Stereoselective differences of central nervous systemdepressive action of a homologous series of 3-alkyl-thalidomide analysis
    • Buech HP, Omlor G, Knabe J. Stereoselective differences of central nervous systemdepressive action of a homologous series of 3-alkyl-thalidomide analysis. Arzneim. Forsch. 40, 32-36 (1990).
    • (1990) Arzneim. Forsch , vol.40 , pp. 32-36
    • Buech, H.P.1    Omlor, G.2    Knabe, J.3
  • 28
    • 0024390578 scopus 로고
    • Synthesis of racemates and enantiomers of 3-alkylthalidomide analogs and determination of their absolute configuration
    • Knabe J, Omlor G. Synthesis of racemates and enantiomers of 3-alkylthalidomide analogs and determination of their absolute configuration. Arch. Der Pharmazie. 322, 499-505 (1989).
    • (1989) Arch. der Pharmazie , vol.322 , pp. 499-505
    • Knabe, J.1    Omlor, G.2
  • 29
    • 77953391866 scopus 로고    scopus 로고
    • Preparation of 4-amino-2-(3-methyl-2,6-dioxopiperidin-3- yl)-isoindole-1,3-dione and compositions thereof for pharmaceutical applications
    • Muller GW, Chen RS. Preparation of 4-amino-2-(3-methyl-2,6- dioxopiperidin-3- yl)-isoindole-1,3-dione and compositions thereof for pharmaceutical applications. PCT Int. Appl. 56 (2006).
    • (2006) PCT Int. Appl. , vol.56
    • Muller, G.W.1    Chen, R.S.2
  • 30
    • 0346887163 scopus 로고    scopus 로고
    • 3-trifluoromethyl- and 3-difluoromethylthalidomides
    • Osipov SN, Tsouker P, Hennig L, Burger K. 3-trifluoromethyl- and 3-difluoromethylthalidomides. Tetrahedron, 60, 271-274 (2004).
    • (2004) Tetrahedron , vol.60 , pp. 271-274
    • Osipov, S.N.1    Tsouker, P.2    Hennig, L.3    Burger, K.4
  • 31
    • 0001093384 scopus 로고    scopus 로고
    • (R)- and (S)-3- fluorothalidomides: Isosteric analogs of thalidomide
    • Takeuchi Y, Shiragami T, Kimura K, Suzuki E, Shibata N. (R)- and (S)-3- fluorothalidomides: isosteric analogs of thalidomide. Org. Lett. 1, 1571-1573 (1999).
    • (1999) Org. Lett. , vol.1 , pp. 1571-1573
    • Takeuchi, Y.1    Shiragami, T.2    Kimura, K.3    Suzuki, E.4    Shibata, N.5
  • 32
    • 77953406859 scopus 로고    scopus 로고
    • Diagnostic compounds comprising a scaffold coupled to a signal entity for medical imaging diagnostic
    • Corot C, Port M, Gautheret T, Williard X. Diagnostic compounds comprising a scaffold coupled to a signal entity for medical imaging diagnostic. US Pat. Appl. Publ. 17 (2005).
    • (2005) US Pat. Appl. Publ. , vol.17
    • Corot, C.1    Port, M.2    Gautheret, T.3    Williard, X.4
  • 33
    • 0034601650 scopus 로고    scopus 로고
    • Thalidomide metabolites and analogs. Part 2: Cyclic derivatives of 2-N-phthalimido- 2S,3S (3-hydroxy) ornithine
    • Luzzio FA, Thomas EM, Figg WD. Thalidomide metabolites and analogs. Part 2: cyclic derivatives of 2-N-phthalimido- 2S,3S (3-hydroxy) ornithine. Tetrahedron Lett. 41, 7151-7155 (2000).
    • (2000) Tetrahedron Lett , vol.41 , pp. 7151-7155
    • Luzzio, F.A.1    Thomas, E.M.2    Figg, W.D.3
  • 34
    • 33845976663 scopus 로고    scopus 로고
    • Efficient asymmetric synthesis of novel 4-substituted and configurationally stable analogs of thalidomide
    • Yamada T, Okada T, Sakaguchi K, Ohfune Y, Ueki H, Soloshonok VA. Efficient asymmetric synthesis of novel 4-substituted and configurationally stable analogs of thalidomide. Org Lett. 8, 5625-5628 (2006)
    • (2006) Org Lett , vol.8 , pp. 5625-5628
    • Yamada, T.1    Okada, T.2    Sakaguchi, K.3    Ohfune, Y.4    Ueki, H.5    Soloshonok, V.A.6
  • 35
    • 0000171574 scopus 로고
    • Fluorine-containing amino acids. III. α-trifluoromethyl-α- amino acids
    • Soloshonok VA, Gerus II, Yagupolskii YL, Kukhar VP. Fluorine-containing amino acids. III. α-trifluoromethyl-α-amino acids. Zh. Org. Khim. 23, 2308-2313 (1987).
    • (1987) Zh. Org. Khim , vol.23 , pp. 2308-2313
    • Soloshonok, V.A.1    Gerus, I.I.2    Yagupolskii, Y.L.3    Kukhar, V.P.4
  • 36
    • 0029163546 scopus 로고
    • Asymmetric aldol reactions of chiral Ni(II)-complex of glycine with aldehydes. Stereodivergent synthesis of syn-(2S)- and syn-(2R)-β- alkylserines
    • Soloshonok VA, Avilov DV, Kukhar VP et al. Asymmetric aldol reactions of chiral Ni(II)-complex of glycine with aldehydes. Stereodivergent synthesis of syn-(2S)- and syn-(2R)-β-alkylserines. Tetra. Asymm. 6, 1741-1756 (1995).
    • (1995) Tetra. Asymm. , vol.6 , pp. 1741-1756
    • Soloshonok, V.A.1    Avilov, D.V.2    Kukhar, V.P.3
  • 37
    • 0029883406 scopus 로고    scopus 로고
    • Kukhar VP Highly diastereoselective asymmetric aldol reactions of chiral Ni(II)-complex of glycine with trifluoromethyl ketones
    • Soloshonok VA, Avilov DV, Kukhar VP Highly diastereoselective asymmetric aldol reactions of chiral Ni(II)-complex of glycine with trifluoromethyl ketones. Tetra. Asymm. 7, 1547-1550 (1996).
    • (1996) Tetra. Asymm. , vol.7 , pp. 1547-1550
    • Soloshonok, V.A.1    Avilov, D.V.2
  • 38
    • 0026520631 scopus 로고
    • A novel approach to the synthesis of symmetric optically active 2,5-dioxopiperazines
    • Basiuk VA, Gromovoy TY, Chuiko AA, Soloshonok VA, Kukhar VP. A novel approach to the synthesis of symmetric optically active 2,5-dioxopiperazines. Synthesis 5, 449-451 (1992).
    • (1992) Synthesis , vol.5 , pp. 449-451
    • Basiuk, V.A.1    Gromovoy, T.Y.2    Chuiko, A.A.3    Soloshonok, V.A.4    Kukhar, V.P.5
  • 39
    • 0027156061 scopus 로고
    • Transamination of fluorinated α-keto carboxylic esters. A biomimetic approach to β-polyfluoroalkyl-β-amino acids
    • Soloshonok VA, Kirilenko AG, Kukhar VP, Resnati G. Transamination of fluorinated α-keto carboxylic esters. A biomimetic approach to β-polyfluoroalkyl-β-amino acids. Tetrahedron Lett. 34, 3621-3624 (1993).
    • (1993) Tetrahedron Lett , vol.34 , pp. 3621-3624
    • Soloshonok, V.A.1    Kirilenko, A.G.2    Kukhar, V.P.3    Resnati, G.4
  • 40
    • 0030592749 scopus 로고    scopus 로고
    • The effect of substituents on the feasibility of azomethine-azomethine isomerization: New synthetic opportunities for biomimetic transamination
    • Soloshonok VA, Ono T. The effect of substituents on the feasibility of azomethine-azomethine isomerization: new synthetic opportunities for biomimetic transamination. Tetrahedron 52, 14701-14712 (1996).
    • (1996) Tetrahedron , vol.52 , pp. 14701-14712
    • Soloshonok, V.A.1    Ono, T.2
  • 42
    • 0028258252 scopus 로고
    • Highly diastereoselective aldol reaction of fluoroalkyl aryl ketones with methyl isocyanoacetate catalyzed by silver(I)/triethylamine
    • Soloshonok VA, Hayashi T, Ishikawa K, Nagashima N. Highly diastereoselective aldol reaction of fluoroalkyl aryl ketones with methyl isocyanoacetate catalyzed by silver(I)/triethylamine. Tetrahedron Lett. 35, 1055-1058 (1994).
    • (1994) Tetrahedron Lett , vol.35 , pp. 1055-1058
    • Soloshonok, V.A.1    Hayashi, T.2    Ishikawa, K.3    Nagashima, N.4
  • 43
    • 0037430440 scopus 로고    scopus 로고
    • Simple and highly diastereoselective synthesis of trifluoromethyl- containing myosmines via reaction between 2-(aminomethyl)pyridine and 1,1,1,5,5,5-hexafluoro-2,4-pentanedione
    • Ohkura H, Berbasov DO, Soloshonok VA. Simple and highly diastereoselective synthesis of trifluoromethyl-containing myosmines via reaction between 2-(aminomethyl)pyridine and 1,1,1,5,5,5-hexafluoro-2,4- pentanedione. Tetrahedron Lett. 44, 2417-2420 (2003).
    • (2003) Tetrahedron Lett , vol.44 , pp. 2417-2420
    • Ohkura, H.1    Berbasov, D.O.2    Soloshonok, V.A.3
  • 44
    • 8544244902 scopus 로고    scopus 로고
    • Stereoselective additions of α-lithiated alkyl p-tolylsulfoxides to N-PMP fluoroalkyl aldimines. An efficient approach to enantiomerically pure fluoro-amino compounds
    • Bravo P, Farina A, Kukhar VP et al. Stereoselective additions of α-lithiated alkyl p-tolylsulfoxides to N-PMP fluoroalkyl aldimines. An efficient approach to enantiomerically pure fluoro-amino compounds J. Org. Chem. 62, 3424-3425 (1997).
    • (1997) J. Org. Chem. , vol.62 , pp. 3424-3425
    • Bravo, P.1    Farina, A.2    Kukhar, V.P.3
  • 45
    • 0000857641 scopus 로고    scopus 로고
    • Transition metal/base-catalyzed aldol reactions of methyl α-isocyanoacetate with prochiral ketones, a straightforward approach to stereochemically defined β,β-disubstituted-β-hydroxy-α- amino acids. Scope and limitations
    • Soloshonok VA, Kacharov AD, Avilov DV, Ishikawa K, Nagashima N, Hayashi T. Transition metal/base-catalyzed aldol reactions of methyl α-isocyanoacetate with prochiral ketones, a straightforward approach to stereochemically defined β,β-disubstituted-β-hydroxy-α- amino acids. Scope and limitations. J. Org. Chem. 62, 3470-3479 (1997).
    • (1997) J. Org. Chem. , vol.62 , pp. 3470-3479
    • Soloshonok, V.A.1    Kacharov, A.D.2    Avilov, D.V.3    Ishikawa, K.4    Nagashima, N.5    Hayashi, T.6
  • 46
    • 0029655532 scopus 로고    scopus 로고
    • Gold(I)-catalyzed asymmetric aldol reactions of isocyanoacetic acid derivatives with fluoroaryl aldehydes
    • Soloshonok VA, Kacharov AD, Hayashi T. Gold(I)-catalyzed asymmetric aldol reactions of isocyanoacetic acid derivatives with fluoroaryl aldehydes. Tetrahedron 52, 245-254 (1996).
    • (1996) Tetrahedron , vol.52 , pp. 245-254
    • Soloshonok, V.A.1    Kacharov, A.D.2    Hayashi, T.3
  • 47
    • 0030945696 scopus 로고    scopus 로고
    • Biomimetic transamination of α-keto perfluorocarboxylic esters. an efficient preparative synthesis of β,β,β-trifluoroalanine
    • Soloshonok VA, Kukhar VP, Biomimetic transamination of α-keto perfluorocarboxylic esters. an efficient preparative synthesis of β,β,β-trifluoroalanine. Tetrahedron 53, 8307-8314 (1997).
    • (1997) Tetrahedron , vol.53 , pp. 8307-8314
    • Soloshonok, V.A.1    Kukhar, V.P.2
  • 48
    • 0001406543 scopus 로고
    • Fluorine-containing amino acids. V. imines of trifluoropyruvic acid in the synthesis of n-substituted trifluoroalanines
    • Soloshonok VA, Yagupolskii YL, Kukhar VP. Fluorine-containing amino acids. V. imines of trifluoropyruvic acid in the synthesis of n-substituted trifluoroalanines. Zh. Org. Khim. 24, 1638-1644 (1988).
    • (1988) Zh. Org. Khim , vol.24 , pp. 1638-1644
    • Soloshonok, V.A.1    Yagupolskii, Y.L.2    Kukhar, V.P.3
  • 49
    • 0034725677 scopus 로고    scopus 로고
    • Convenient asymmetric synthesis of enantiomerically pure 2́6́-dimethyltyrosine (DMT) via alkylation of chiral nucleophilic glycine equivalent
    • Tang X, Soloshonok VA, Hruby VJ. Convenient asymmetric synthesis of enantiomerically pure 2́6́-dimethyltyrosine (DMT) via alkylation of chiral nucleophilic glycine equivalent. Tetra. Asymm. 11, 2917-2925 (2000).
    • (2000) Tetra. Asymm. , vol.11 , pp. 2917-2925
    • Tang, X.1    Soloshonok, V.A.2    Hruby, V.J.3
  • 50
    • 0035939193 scopus 로고    scopus 로고
    • Large-scale asymmetric synthesis of novel sterically constrained 2́,6́-dimethyl- and α,2́,6́-trimethyltyrosine and -phenylalanine derivatives via alkylation of chiral equivalents of nucleophilic glycine and alanine
    • Soloshonok VA, Tang X, Hruby VJ. Large-scale asymmetric synthesis of novel sterically constrained 2́,6́-dimethyl- and α,2́,6́-trimethyltyrosine and -phenylalanine derivatives via alkylation of chiral equivalents of nucleophilic glycine and alanine. Tetrahedron 57, 6375-6382 (2001).
    • (2001) Tetrahedron , vol.57 , pp. 6375-6382
    • Soloshonok, V.A.1    Tang, X.2    Hruby, V.J.3
  • 51
    • 0043032849 scopus 로고    scopus 로고
    • Efficient synthesis of sterically constrained symmetrically α,α-disubstituted α-amino acids under operationally convenient conditions
    • Ellis TK, Martin CH, Tsai GM, Ueki H, Soloshonok VA. Efficient synthesis of sterically constrained symmetrically α,α-disubstituted α-amino acids under operationally convenient conditions. J. Org. Chem. 68, 6208-6214 (2003).
    • (2003) J. Org. Chem , vol.68 , pp. 6208-6214
    • Ellis, T.K.1    Martin, C.H.2    Tsai, G.M.3    Ueki, H.4    Soloshonok, V.A.5
  • 52
    • 0035825086 scopus 로고    scopus 로고
    • Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics
    • Qiu W, Gu X, Soloshonok VA, Carducci MD, Hruby VJ. Stereoselective synthesis of conformationally constrained reverse turn dipeptide mimetics. Tetrahedron Lett. 42, 145-148 (2001).
    • (2001) Tetrahedron Lett , vol.42 , pp. 145-148
    • Qiu, W.1    Gu, X.2    Soloshonok, V.A.3    Carducci, M.D.4    Hruby, V.J.5
  • 53
    • 1542725948 scopus 로고    scopus 로고
    • Biological and conformational study of β-substituted prolines in MT-II template: Steric effects leading to human MC5 receptor selectivity
    • Cai M, Cai C, Mayorov AV et al. Biological and conformational study of β-substituted prolines in MT-II template: steric effects leading to human MC5 receptor selectivity. J. Peptide Res. 63, 116-131 (2004).
    • (2004) J. Peptide Res. , vol.63 , pp. 116-131
    • Cai, M.1    Cai, C.2    Mayorov, A.V.3
  • 54
    • 0035825745 scopus 로고    scopus 로고
    • Meervelt LV. asymmetric synthesis of α,β-dialkyl- αphenylalanines via direct alkylation of chiral alanine derivative with racemic α-alkylbenzylbromides. A case of high enantiomer differentiation at room temperature
    • Soloshonok VA, Tang X, Hruby VJ, Meervelt LV. asymmetric synthesis of α,β-dialkyl-αphenylalanines via direct alkylation of chiral alanine derivative with racemic α-alkylbenzylbromides. A case of high enantiomer differentiation at room temperature. Org. Lett. 3, 341-343 (2001).
    • (2001) Org. Lett. , vol.3 , pp. 341-343
    • Soloshonok, V.A.1    Tang, X.2    Hruby, V.J.3
  • 55
    • 0028329208 scopus 로고
    • Gold(I)-catalyzed asymmetric aldol reaction of methyl isocyanoacetate with fluorinated benzaldehydes
    • Soloshonok VA, Hayashi T. Gold(I)-catalyzed asymmetric aldol reaction of methyl isocyanoacetate with fluorinated benzaldehydes. Tetrahedron Lett. 35, 2713-2716 (1994).
    • (1994) Tetrahedron Lett , vol.35 , pp. 2713-2716
    • Soloshonok, V.A.1    Hayashi, T.2
  • 57
    • 0033536721 scopus 로고    scopus 로고
    • Asymmetric michael addition reactions of chiral Ni(II) complex of glycine with N-(enoyl)oxazolidinones: Improved reactivity and stereochemical outcome
    • Soloshonok VA, Cai C, Hruby VJ. Asymmetric michael addition reactions of chiral Ni(II) complex of glycine with N-(enoyl)oxazolidinones: improved reactivity and stereochemical outcome. Tetrahedron 55, 12031-12044 (1999).
    • (1999) Tetrahedron , vol.55 , pp. 12031-12044
    • Soloshonok, V.A.1    Cai, C.2    Hruby, V.J.3
  • 58
    • 0033536604 scopus 로고    scopus 로고
    • Asymmetric synthesis of novel highly sterically constrained (2S,3S)-3-methyl-3-trifluoromethyl- and (2S,3S,4R)-3-trifluoromethyl-4- methylpyroglutamic acids
    • Soloshonok VA, Cai C, Hruby VJ, Meervelt LV. Asymmetric synthesis of novel highly sterically constrained (2S,3S)-3-methyl-3-trifluoromethyl- and (2S,3S,4R)-3-trifluoromethyl-4- methylpyroglutamic acids. Tetrahedron 55, 12045-12058 (1999).
    • (1999) Tetrahedron , vol.55 , pp. 12045-12058
    • Soloshonok, V.A.1    Cai, C.2    Hruby, V.J.3    Meervelt, L.V.4
  • 59
    • 0042338452 scopus 로고    scopus 로고
    • Improved synthesis of proline derived Ni(II)-complexes of glycine, a versatile chiral equivalents of nucleophilic glycine for general asymmetric synthesis of α-amino acids
    • Ueki H, Ellis TK, Martin CH, Bolene SB, Boettiger TU, Soloshonok VA. Improved synthesis of proline derived Ni(II)-complexes of glycine, a versatile chiral equivalents of nucleophilic glycine for general asymmetric synthesis of α-amino acids. J. Org. Chem. 68, 7104-7107 (2003).
    • (2003) J. Org. Chem , vol.68 , pp. 7104-7107
    • Ueki, H.1    Ellis, T.K.2    Martin, C.H.3    Bolene, S.B.4    Boettiger, T.U.5    Soloshonok, V.A.6
  • 60
    • 27544463710 scopus 로고    scopus 로고
    • Michael addition reactions between chiral equivalents of a nucleophilic glycine and (S)- or (R)-3-(Eenoyl)- 4-phenyl-1,3-oxazolidin-2-ones as a general method for efficient preparation of β-substituted pyroglutamic acids. Case of topographically controlled stereoselectivity
    • Soloshonok VA, Cai C, Yamada T, Ueki H, Ohfune Y, Hruby VJ. Michael addition reactions between chiral equivalents of a nucleophilic glycine and (S)- or (R)-3-(Eenoyl)- 4-phenyl-1,3-oxazolidin-2-ones as a general method for efficient preparation of β-substituted pyroglutamic acids. Case of topographically controlled stereoselectivity. J. Am. Chem. Soc. 127, 15296-15303 (2005).
    • (2005) J. Am. Chem. Soc , vol.127 , pp. 15296-15303
    • Soloshonok, V.A.1    Cai, C.2    Yamada, T.3    Ueki, H.4    Ohfune, Y.5    Hruby, V.J.6
  • 61
    • 0036224968 scopus 로고    scopus 로고
    • Highly diastereoselective michael addition reactions between nucleophilic glycine equivalents and β-substituted-α,β-unsaturated carboxylic acid derivatives; A general approach to the stereochemically defined and sterically γ-constrained α-amino acids
    • Soloshonok VA. Highly diastereoselective michael addition reactions between nucleophilic glycine equivalents and β-substituted-α,β- unsaturated carboxylic acid derivatives; a general approach to the stereochemically defined and sterically γ-constrained α-amino acids. Current Org. Chem. 6, 341-364 (2002).
    • (2002) Current Org. Chem. , vol.6 , pp. 341-364
    • Soloshonok, V.A.1
  • 62
    • 37049079441 scopus 로고
    • Asymmetric synthesis of phosphorus analogs of dicarboxylic α-amino acids
    • Soloshonok VA, Belokon YN, Kuzmina NA et al. Asymmetric synthesis of phosphorus analogs of dicarboxylic α-amino acids. J. Chem. Soc. Perkin Trans. 1, 1525-1529 (1992).
    • (1992) J. Chem. Soc. Perkin Trans , vol.1 , pp. 1525-1529
    • Soloshonok, V.A.1    Belokon, Y.N.2    Kuzmina, N.A.3
  • 63
    • 0034704633 scopus 로고    scopus 로고
    • (S)- or (R)-N-(E-enoyl)-4-phenyl-1,3-oxazolidin-2- ones: Ideal michael acceptors to afford a virtually complete control of simple and face diastereoselectivity in addition reactions with glycine derivatives
    • Soloshonok VA, Cai C, Hruby VJ. (S)- or (R)-N-(E-enoyl)-4-phenyl-1,3- oxazolidin-2- ones: ideal michael acceptors to afford a virtually complete control of simple and face diastereoselectivity in addition reactions with glycine derivatives. Org. Lett. 2, 747-750 (2000).
    • (2000) Org. Lett. , vol.2 , pp. 747-750
    • Soloshonok, V.A.1    Cai, C.2    Hruby, V.J.3
  • 64
    • 0034620199 scopus 로고    scopus 로고
    • Toward design of a practical methodology for stereocontrolled synthesis of γ-constrained pyroglutamic acids and related compounds. virtually complete control of simple diastereoselectivity in the michael addition reactions of glycine Ni(II) complexes with N-(enoyl)oxazolidinones
    • Soloshonok VA, Cai C, Hruby VJ. Toward design of a practical methodology for stereocontrolled synthesis of γ-constrained pyroglutamic acids and related compounds. virtually complete control of simple diastereoselectivity in the michael addition reactions of glycine Ni(II) complexes with N-(enoyl)oxazolidinones. Tetrahedron Lett. 41, 135-139 (2000).
    • (2000) Tetrahedron Lett , vol.41 , pp. 135-139
    • Soloshonok, V.A.1    Cai, C.2    Hruby, V.J.3
  • 65
    • 0034598019 scopus 로고    scopus 로고
    • A unique case of face diastereoselectivity in the michael addition reactions between Ni(II)-complexes of glycine and chiral 3-(E-enoyl)-1,3- oxazolidin- 2-ones
    • Soloshonok VA, Cai C, Hruby VJ. A unique case of face diastereoselectivity in the michael addition reactions between Ni(II)-complexes of glycine and chiral 3-(E-enoyl)-1,3-oxazolidin- 2-ones. Tetrahedron Lett. 41, 9645-9649 (2000).
    • (2000) Tetrahedron Lett , vol.41 , pp. 9645-9649
    • Soloshonok, V.A.1    Cai, C.2    Hruby, V.J.3
  • 66
    • 0033402142 scopus 로고    scopus 로고
    • Asymmetric michael addition reactions of chiral Ni(II) complex of glycine with N-(enoyl)oxazolidinones: Improved reactivity and stereochemical outcome
    • Soloshonok VA, Cai C, Hruby VJ. Asymmetric michael addition reactions of chiral Ni(II) complex of glycine with N-(enoyl)oxazolidinones: improved reactivity and stereochemical outcome. Tetra. Asymm. 10, 4265-4269 (1999).
    • (1999) Tetra. Asymm. , vol.10 , pp. 4265-4269
    • Soloshonok, V.A.1    Cai, C.2    Hruby, V.J.3
  • 67
    • 12344332239 scopus 로고    scopus 로고
    • New generation of nucleophilic glycine equivalents
    • Soloshonok VA, Ueki H, Ellis TK. New generation of nucleophilic glycine equivalents. Tetrahedron Lett. 46, 941-944 (2005).
    • (2005) Tetrahedron Lett , vol.46 , pp. 941-944
    • Soloshonok, V.A.1    Ueki, H.2    Ellis, T.K.3
  • 68
    • 12444311634 scopus 로고    scopus 로고
    • Application of modular nucleophilic glycine equivalents for truly practical asymmetric synthesis of β-substituted pyroglutamic acids
    • Soloshonok VA, Ueki H, Ellis TK, Yamada T, Ohfune Y. Application of modular nucleophilic glycine equivalents for truly practical asymmetric synthesis of β-substituted pyroglutamic acids. Tetrahedron Lett. 46, 1107-1110 (2005).
    • (2005) Tetrahedron Lett , vol.46 , pp. 1107-1110
    • Soloshonok, V.A.1    Ueki, H.2    Ellis, T.K.3    Yamada, T.4    Ohfune, Y.5
  • 69
    • 33644991932 scopus 로고    scopus 로고
    • Design and synthesis of a new generation of 'NH' Ni(II) complexes of glycine schiff bases and their unprecedented C-H vs. N-H chemoselectivity in the alkyl halide alkylations and Michael addition reactions
    • Soloshonok VA, Ellis TK. Design and synthesis of a new generation of 'NH' Ni(II) complexes of glycine schiff bases and their unprecedented C-H vs. N-H chemoselectivity in the alkyl halide alkylations and Michael addition reactions. Synlett 533-538 (2006).
    • (2006) Synlett , pp. 533-538
    • Soloshonok, V.A.1    Ellis, T.K.2
  • 70
    • 33750437425 scopus 로고    scopus 로고
    • The design, synthesis and evaluation of a new generation of modular nucleophilic glycine equivalents for the efficient synthesis of sterically constrained α-amino acids
    • Ellis TK, Ueki H, Yamada T, Ohfune Y, Soloshonok VA. The design, synthesis and evaluation of a new generation of modular nucleophilic glycine equivalents for the efficient synthesis of sterically constrained α-amino acids. J. Org. Chem. 71, 8572-8578 (2006).
    • (2006) J. Org. Chem. , vol.71 , pp. 8572-8578
    • Ellis, T.K.1    Ueki, H.2    Yamada, T.3    Ohfune, Y.4    Soloshonok, V.A.5
  • 71
    • 0036942301 scopus 로고    scopus 로고
    • A convenient, room temperatureorganic base protocol for preparing chiral N-(enoyl)-1,3-oxazolidine-2-ones
    • Soloshonok VA, Ueki H, Jiang C, Cai C, Hruby VJ. A convenient, room temperatureorganic base protocol for preparing chiral N-(enoyl)-1,3-oxazolidine- 2-ones. Helv. Chim. Acta. 85, 3616-3623 (2002).
    • (2002) Helv. Chim. Acta. , vol.85 , pp. 3616-3623
    • Soloshonok, V.A.1    Ueki, H.2    Jiang, C.3    Cai, C.4    Hruby, V.J.5
  • 72
    • 0002432346 scopus 로고    scopus 로고
    • Michael addition of organocopper species to 3-[(E)-4, 4,4-trifluorobut-2-enoyl] oxazolidin-2-ones
    • Yamazaki T, Shinohara N, Kitazume T, Sato S. Michael addition of organocopper species to 3-[(E)-4,4,4-trifluorobut-2-enoyl] oxazolidin-2-ones. J. Fluorine Chem. 97, 91-96 (1999).
    • (1999) J. Fluorine Chem. , vol.97 , pp. 91-96
    • Yamazaki, T.1    Shinohara, N.2    Kitazume, T.3    Sato, S.4
  • 73
    • 0035936788 scopus 로고    scopus 로고
    • Michael addition reactions between chiral Ni(II) complex of glycine and 3-(trans-enoyl) oxazolidin-2-ones. A case of electron donor-acceptor attractive interactionscontrolled face diastereoselectivity
    • Cai C, Soloshonok VA, Hruby VJ. Michael addition reactions between chiral Ni(II) complex of glycine and 3-(trans-enoyl) oxazolidin-2-ones. A case of electron donor-acceptor attractive interactionscontrolled face diastereoselectivity. J. Org. Chem. 66, 1339-1350 (2001).
    • (2001) J. Org. Chem. , vol.66 , pp. 1339-1350
    • Cai, C.1    Soloshonok, V.A.2    Hruby, V.J.3
  • 75
    • 0028307422 scopus 로고
    • Gold(I)- catalyzed asymmetric aldol reaction of fluorinated benzaldehydes with α-isocyanoacetamide
    • Soloshonok VA, Hayashi T. Gold(I)- catalyzed asymmetric aldol reaction of fluorinated benzaldehydes with α-isocyanoacetamide. Tetra. Asymm. 5, 1091-1094 (1994).
    • (1994) Tetra. Asymm. , vol.5 , pp. 1091-1094
    • Soloshonok, V.A.1    Hayashi, T.2
  • 76
    • 4744338689 scopus 로고    scopus 로고
    • Hetero-Diels-Alder and pyroglutamate approaches to (2S,4R)-2-methylamino- 5- hydroxy-4-methylpentanoic acid
    • Tarver JE, Terranove KM, Joullie MM. Hetero-Diels-Alder and pyroglutamate approaches to (2S,4R)-2-methylamino-5- hydroxy-4-methylpentanoic acid. Tetrahedron 45, 10277-10284 (2004).
    • (2004) Tetrahedron , vol.45 , pp. 10277-10284
    • Tarver, J.E.1    Terranove, K.M.2    Joullie, M.M.3
  • 77
    • 37049148514 scopus 로고
    • New synthesis of glutamine and of γ-dipeptides of glutamic acid from phthalylated intermediates
    • King FE, Kidd DAA. New synthesis of glutamine and of γ-dipeptides of glutamic acid from phthalylated intermediates. J. Chem. Soc. 3315-3319 (1949).
    • (1949) J. Chem. Soc. , pp. 3315-3319
    • King, F.E.1    Kidd, D.A.A.2
  • 78
    • 0026701551 scopus 로고
    • The synthesis of syn- and anti-2(S)-phthalimidomethyl-2,3,4,4α,7, 7αhexahydro- 6-oxo-5H-pyrano[2,3-β]pyrroles as rigid β-bend peptide-mimetics
    • Krstenansky JL, del Rosario-Chow M, Currie BL. The synthesis of syn- and anti-2(S)-phthalimidomethyl-2,3,4,4α,7,7αhexahydro- 6-oxo-5H-pyrano[2,3-β]pyrroles as rigid β-bend peptide-mimetics. J. Heterocyclic Chem. 29, 707-711 (1992).
    • (1992) J. Heterocyclic Chem. , vol.29 , pp. 707-711
    • Krstenansky, J.L.1    Del Rosario-Chow, M.2    Currie, B.L.3
  • 79
    • 0025356803 scopus 로고
    • Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protecting groups via tert-butyldimethylsilyl carbamates
    • Sakaitani M, Ohfune Y. Syntheses and reactions of silyl carbamates. 1. Chemoselective transformation of amino protecting groups via tert-butyldimethylsilyl carbamates. J. Org. Chem. 55, 870-876 (1990).
    • (1990) J. Org. Chem. , vol.55 , pp. 870-876
    • Sakaitani, M.1    Ohfune, Y.2
  • 80
    • 0033532216 scopus 로고    scopus 로고
    • An expeditious synthesis of cyclic imides
    • Flaih N, Pharm-Huy C, Galons H. An expeditious synthesis of cyclic imides. Tetrahedron Lett. 40, 3697-3698 (1999).
    • (1999) Tetrahedron Lett , vol.40 , pp. 3697-3698
    • Flaih, N.1    Pharm-Huy, C.2    Galons, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.