메뉴 건너뛰기




Volumn 17, Issue 1, 2013, Pages 29-42

Studies directed towards anthracyclinone syntheses: The use of d-glucose as a chiral auxiliary in asymmetric Diels-Alder reactions

Author keywords

Anthracycline; Anthracyclinone; Asymmetric Diels Alder reactions; Chemotherapy; D Glucose auxiliary; Intercalation; Semi empirical (MNDO) HOMO LUMO energy gaps; Silyloxy dienes; SPARTAN'08; Stereoselective synthesis

Indexed keywords


EID: 84871698981     PISSN: 13196103     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jscs.2011.02.019     Document Type: Article
Times cited : (7)

References (59)
  • 2
    • 33947717002 scopus 로고    scopus 로고
    • Anticancer drugs from nature - natural products as a unique source of new microtubule-stabilizing agents
    • Altmann K.-H., Gertsch J. Anticancer drugs from nature - natural products as a unique source of new microtubule-stabilizing agents. Nat. Prod. Rep. 2007, 24:327-357.
    • (2007) Nat. Prod. Rep. , vol.24 , pp. 327-357
    • Altmann, K.-H.1    Gertsch, J.2
  • 5
    • 37049071842 scopus 로고
    • Asymmetric Diels-Alder reactions. Part 6. Regio- and stereo-selective cycloadditions of 5-(2',3',4',6'-tetra-O-acetyl-β-d-glucopyranosyloxy)-1,4-naphthoquinone
    • Beagley B., Curtis A.D.M., Pritchard R.G., Stoodley R.J. Asymmetric Diels-Alder reactions. Part 6. Regio- and stereo-selective cycloadditions of 5-(2',3',4',6'-tetra-O-acetyl-β-d-glucopyranosyloxy)-1,4-naphthoquinone. J. Chem. Soc., Perkin Trans. 1 1992, 1981-1991.
    • (1992) J. Chem. Soc., Perkin Trans. 1 , pp. 1981-1991
    • Beagley, B.1    Curtis, A.D.M.2    Pritchard, R.G.3    Stoodley, R.J.4
  • 6
    • 2442700673 scopus 로고    scopus 로고
    • Enantioselective synthesis of (+)-8-hydroxy-8-methylidarubicinone
    • Bourghli L.M.S., Stoodley R.J. Enantioselective synthesis of (+)-8-hydroxy-8-methylidarubicinone. Bioorg. Med. Chem. 2004, 12:2863-2866.
    • (2004) Bioorg. Med. Chem. , vol.12 , pp. 2863-2866
    • Bourghli, L.M.S.1    Stoodley, R.J.2
  • 7
    • 34250850813 scopus 로고    scopus 로고
    • The intercalation of DNA double helices with doxorubicin and nagalomycin
    • Box V.G.S. The intercalation of DNA double helices with doxorubicin and nagalomycin. J. Mol. Graph. Modell. 2007, 26:14-19.
    • (2007) J. Mol. Graph. Modell. , vol.26 , pp. 14-19
    • Box, V.G.S.1
  • 8
    • 1542497253 scopus 로고
    • über Tetraoxy-dibenzo-thianthrendichinon; mit einem Beitrag zur Chemie des Naphthazarins
    • Brass K., Pfluger R., Honsberg K. über Tetraoxy-dibenzo-thianthrendichinon; mit einem Beitrag zur Chemie des Naphthazarins. Chem. Ber. 1936, 69:80-87.
    • (1936) Chem. Ber. , vol.69 , pp. 80-87
    • Brass, K.1    Pfluger, R.2    Honsberg, K.3
  • 9
    • 0009503761 scopus 로고
    • Daunomycin: a new antibiotic with cytostatic activity; isolation and properties
    • Cassinelli G., Orezzi P. Daunomycin: a new antibiotic with cytostatic activity; isolation and properties. Giorn. Microbiol. 1963, 11:167-174.
    • (1963) Giorn. Microbiol. , vol.11 , pp. 167-174
    • Cassinelli, G.1    Orezzi, P.2
  • 10
  • 12
    • 37049103189 scopus 로고
    • 4a,9a-Epoxy-4a,9a-dihydroanthracene-1,4,9,10-tetrone: a versatile synthon in anthracyclinone synthesis
    • Chandler M., Stoodley R.J. 4a,9a-Epoxy-4a,9a-dihydroanthracene-1,4,9,10-tetrone: a versatile synthon in anthracyclinone synthesis. J. Chem. Soc., Chem. Commun. 1978, 997-998.
    • (1978) J. Chem. Soc., Chem. Commun. , pp. 997-998
    • Chandler, M.1    Stoodley, R.J.2
  • 13
    • 0027294721 scopus 로고
    • Unusual allylic acetoxylations of silyl enol ethers with lead(IV) acetate
    • Crilley M.M.L., Larsen D.S., Stoodley R.J., Tomé F. Unusual allylic acetoxylations of silyl enol ethers with lead(IV) acetate. Tetrahedron Lett. 1993, 34:3305-3308.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 3305-3308
    • Crilley, M.M.L.1    Larsen, D.S.2    Stoodley, R.J.3    Tomé, F.4
  • 14
    • 84871703532 scopus 로고    scopus 로고
    • CS CHEM3D, Pro®, Version 5, Cambridge Soft Corporation, Cambridge, MA.
    • CS CHEM3D, 1999. Pro®, Version 5, Cambridge Soft Corporation, Cambridge, MA.
    • (1999)
  • 15
    • 84871707689 scopus 로고
    • The Development of Sugar-Based Quinones for Asymmetric Synthesis.
    • Doctoral Thesis University of Manchester
    • Curtis, A.D.M., 1991. The Development of Sugar-Based Quinones for Asymmetric Synthesis. Doctoral Thesis, University of Manchester.
    • (1991)
    • Curtis, A.D.M.1
  • 16
    • 0018784174 scopus 로고
    • Diels-Alder reactions of trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene
    • Danishefsky S., Kitahara T., Yan C.F., Morris J. Diels-Alder reactions of trans-1-methoxy-3-trimethylsilyloxy-1,3-butadiene. J. Am. Chem. Soc. 1979, 101:6996-7000.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 6996-7000
    • Danishefsky, S.1    Kitahara, T.2    Yan, C.F.3    Morris, J.4
  • 17
    • 0029001279 scopus 로고
    • A trigonal form of the idarubicin:d(CGATCG) complex; crystal and molecular structure at 2.0å resolution
    • Dautant A., Langlois d'Estaintot B., Gallois B., Brown T., Hunter W.N. A trigonal form of the idarubicin:d(CGATCG) complex; crystal and molecular structure at 2.0å resolution. Nucleic Acids Res. 1995, 23:1710-1716.
    • (1995) Nucleic Acids Res. , vol.23 , pp. 1710-1716
    • Dautant, A.1    Langlois d'Estaintot, B.2    Gallois, B.3    Brown, T.4    Hunter, W.N.5
  • 18
    • 84962105974 scopus 로고
    • Synthesen in der hydroaromatischen Reihe
    • Diels O., Alder K. Synthesen in der hydroaromatischen Reihe. Justus Liebigs Ann. Chem. 1928, 460:98-122.
    • (1928) Justus Liebigs Ann. Chem. , vol.460 , pp. 98-122
    • Diels, O.1    Alder, K.2
  • 19
  • 22
    • 0036024586 scopus 로고    scopus 로고
    • Combination of taxanes and anthracyclines in first-line chemotherapy of metastatic breast cancer: an interim report
    • Friedrichs K., Hölzel F., Jänicke F. Combination of taxanes and anthracyclines in first-line chemotherapy of metastatic breast cancer: an interim report. Eur. J. Cancer 2002, 38:1730-1738.
    • (2002) Eur. J. Cancer , vol.38 , pp. 1730-1738
    • Friedrichs, K.1    Hölzel, F.2    Jänicke, F.3
  • 24
    • 84871673913 scopus 로고    scopus 로고
    • Syntezy naturalnych i modyfikowanych antybiotykow antracyklinowych ze wspolnego prekursora. WiadomoŚci Chemiczne 56
    • Grynkiewicz, G., Achmatowicz, O., Fokt, I., Priebe, W., Ramza, J., Szechner, B., Szeja, W., 2002. Syntezy naturalnych i modyfikowanych antybiotykow antracyklinowych ze wspolnego prekursora. WiadomoŚci Chemiczne 56, 535-560.
    • (2002) , pp. 535-560
    • Grynkiewicz, G.1    Achmatowicz, O.2    Fokt, I.3    Priebe, W.4    Ramza, J.5    Szechner, B.6    Szeja, W.7
  • 25
    • 0021717033 scopus 로고
    • An Efficient enantiocontrolled synthesis of (+)-4-demethoxydaunomycinone
    • Gupta R.C., Harland P.A., Stoodley R.J. An Efficient enantiocontrolled synthesis of (+)-4-demethoxydaunomycinone. Tetrahedron 1984, 40:4657-4667.
    • (1984) Tetrahedron , vol.40 , pp. 4657-4667
    • Gupta, R.C.1    Harland, P.A.2    Stoodley, R.J.3
  • 27
    • 37049067030 scopus 로고
    • Asymmetric Diels-Alder reactions. Part 1. Diastereofacial reactivity of (E)-3-trimethylsilyloxybutyl-1,3-dienyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside towards cyclic dienophiles
    • Gupta R.C., Raynor C.M., Stoodley R.J., Slawin A.M.Z., Williams D.J. Asymmetric Diels-Alder reactions. Part 1. Diastereofacial reactivity of (E)-3-trimethylsilyloxybutyl-1,3-dienyl 2,3,4,6-tetra-O-acetyl-β-d-glucopyranoside towards cyclic dienophiles. J. Chem. Soc., Perkin Trans. 1 1988, 1773-1785.
    • (1988) J. Chem. Soc., Perkin Trans. 1 , pp. 1773-1785
    • Gupta, R.C.1    Raynor, C.M.2    Stoodley, R.J.3    Slawin, A.M.Z.4    Williams, D.J.5
  • 28
    • 51149213708 scopus 로고
    • Asymmetric Diels-Alder reactions. Part 2. A model to account for the diastereofacial reactivity of (E)-1-(2',3',4',6'-tetra-O-acetyl-β-d-glucopyranosyloxy)-3-trimethylsiloxybuta-1,3-diene and its 2-methyl derivative
    • Gupta R.C., Larsen D.S., Stoodley R.J., Slawin A.M.Z., Williams D.J. Asymmetric Diels-Alder reactions. Part 2. A model to account for the diastereofacial reactivity of (E)-1-(2',3',4',6'-tetra-O-acetyl-β-d-glucopyranosyloxy)-3-trimethylsiloxybuta-1,3-diene and its 2-methyl derivative. J. Chem. Soc., Perkin Trans. 1 1989, 739-749.
    • (1989) J. Chem. Soc., Perkin Trans. 1 , pp. 739-749
    • Gupta, R.C.1    Larsen, D.S.2    Stoodley, R.J.3    Slawin, A.M.Z.4    Williams, D.J.5
  • 29
    • 0038990567 scopus 로고
    • Alkylations at the γ-position of acetoacetaldehyde and α-benzylacetoacetaldehyde through their dicarbanions
    • Harris T.M., Boatman S., Hauser C.R. Alkylations at the γ-position of acetoacetaldehyde and α-benzylacetoacetaldehyde through their dicarbanions. J. Am. Chem. Soc. 1963, 85:3273-3276.
    • (1963) J. Am. Chem. Soc. , vol.85 , pp. 3273-3276
    • Harris, T.M.1    Boatman, S.2    Hauser, C.R.3
  • 30
    • 0030772585 scopus 로고    scopus 로고
    • Synthetic studies with carbohydrate-derived chiral auxiliaries
    • Hultin P.G., Earle M.A., Sudharshan M. Synthetic studies with carbohydrate-derived chiral auxiliaries. Tetrahedron 1997, 53:14823-14870.
    • (1997) Tetrahedron , vol.53 , pp. 14823-14870
    • Hultin, P.G.1    Earle, M.A.2    Sudharshan, M.3
  • 31
    • 0017189684 scopus 로고
    • Studies directed toward the synthesis of adriamycin: Diels-Alder reactions of anthradiquinones and various dienes
    • Kelly T.R., Goerner R.N., Gillard J.W., Prazak B.K. Studies directed toward the synthesis of adriamycin: Diels-Alder reactions of anthradiquinones and various dienes. Tetrahedron Lett. 1976, 43:3869-3872.
    • (1976) Tetrahedron Lett. , vol.43 , pp. 3869-3872
    • Kelly, T.R.1    Goerner, R.N.2    Gillard, J.W.3    Prazak, B.K.4
  • 32
    • 0036158328 scopus 로고    scopus 로고
    • Enantioselective synthesis of (+)-4-demethoxy-1,4-dimethyldaunomycinone
    • Kotha S., Stoodley R.J. Enantioselective synthesis of (+)-4-demethoxy-1,4-dimethyldaunomycinone. Bioorg. Med. Chem. 2002, 10:621-624.
    • (2002) Bioorg. Med. Chem. , vol.10 , pp. 621-624
    • Kotha, S.1    Stoodley, R.J.2
  • 33
    • 0022785312 scopus 로고
    • Total synthesis of anthracyclinone
    • Krohn K. Total synthesis of anthracyclinone. Angew. Chem., Int. Ed. Engl. 1986, 25:790-807.
    • (1986) Angew. Chem., Int. Ed. Engl. , vol.25 , pp. 790-807
    • Krohn, K.1
  • 34
    • 0018672545 scopus 로고
    • 1. Totalsynthese des daunomycinons
    • 1. Totalsynthese des daunomycinons. Chem. Ber. 1979, 112:3453-3471.
    • (1979) Chem. Ber. , vol.112 , pp. 3453-3471
    • Krohn, K.1    Tolkiehn, H.2
  • 35
    • 37049079494 scopus 로고
    • Asymmetric Diels-Alder reactions. Part 3. Influence of butadiene structure upon the diastereofacial reactivity of (E)-1-(2',3',4',6'-tetra-O-acetyl-β-d-glucopyranosyloxy)buta-1,3-dienes
    • Larsen D.S., Stoodley R.J. Asymmetric Diels-Alder reactions. Part 3. Influence of butadiene structure upon the diastereofacial reactivity of (E)-1-(2',3',4',6'-tetra-O-acetyl-β-d-glucopyranosyloxy)buta-1,3-dienes. J. Chem. Soc., Perkin Trans. 1 1989, 1841-1852.
    • (1989) J. Chem. Soc., Perkin Trans. 1 , pp. 1841-1852
    • Larsen, D.S.1    Stoodley, R.J.2
  • 36
    • 77954244845 scopus 로고    scopus 로고
    • Highly enantioselective formal aza-Diels-Alder reactions with acylhydrazones and Danishefsky's diene promoted by a silicon Lewis acid
    • Lee S.K., Tambar U.K., Perl N.R., Leighton J.L. Highly enantioselective formal aza-Diels-Alder reactions with acylhydrazones and Danishefsky's diene promoted by a silicon Lewis acid. Tetrahedron 2010, 66:4769-4774.
    • (2010) Tetrahedron , vol.66 , pp. 4769-4774
    • Lee, S.K.1    Tambar, U.K.2    Perl, N.R.3    Leighton, J.L.4
  • 37
    • 84871673895 scopus 로고
    • Asymmetric Synthesis of Anticancer Anthracyclines. Doctoral Thesis, University of Manchester
    • Miller, J.P., 1994. Asymmetric Synthesis of Anticancer Anthracyclines. Doctoral Thesis, University of Manchester.
    • (1994)
    • Miller, J.P.1
  • 38
    • 79958276147 scopus 로고    scopus 로고
    • press. The use of d-glucose-based silyloxy dienes in anthracyclinone synthesis. J. Saudi Chem. Soc.
    • Miller, J.P., Stoodley, R.J., in press. The use of d-glucose-based silyloxy dienes in anthracyclinone synthesis. J. Saudi Chem. Soc., doi:10.1016/j.jscs.2010.10.004.
    • Miller, J.P.1    Stoodley, R.J.2
  • 39
    • 34548091847 scopus 로고    scopus 로고
    • Effects of patupilone (epothilone B; EP0906), a novel chemotherapeutic agent, in hepatocellular carcinoma: an in vitro study
    • Mok T.S., Choi E., Yau D., Johri A., Yeo W., Chan A.T., Wong C. Effects of patupilone (epothilone B; EP0906), a novel chemotherapeutic agent, in hepatocellular carcinoma: an in vitro study. Oncology 2006, 71:292-296.
    • (2006) Oncology , vol.71 , pp. 292-296
    • Mok, T.S.1    Choi, E.2    Yau, D.3    Johri, A.4    Yeo, W.5    Chan, A.T.6    Wong, C.7
  • 40
    • 0035357574 scopus 로고    scopus 로고
    • Recent developments in the field of antitumour anthracyclines
    • Monneret C. Recent developments in the field of antitumour anthracyclines. Eur. J. Med. Chem. 2001, 36:483-493.
    • (2001) Eur. J. Med. Chem. , vol.36 , pp. 483-493
    • Monneret, C.1
  • 41
    • 78751528133 scopus 로고    scopus 로고
    • Donor-acceptor substituted phenylethynyltriphenylenes - excited state intramolecular charge transfer, solvatochromic absorption and fluorescence emission
    • Nandy R., Sankararaman S. Donor-acceptor substituted phenylethynyltriphenylenes - excited state intramolecular charge transfer, solvatochromic absorption and fluorescence emission. Beilstein. J. Org. Chem. 2010, 6:992-1001.
    • (2010) Beilstein. J. Org. Chem. , vol.6 , pp. 992-1001
    • Nandy, R.1    Sankararaman, S.2
  • 43
    • 33749658984 scopus 로고    scopus 로고
    • Asymmetric aza-Diels-Alder reaction of Danishefsky's diene with imines in a chiral reaction medium
    • Pégot B., Van Buu O.N., Gori D., Vo-Thanh G. Asymmetric aza-Diels-Alder reaction of Danishefsky's diene with imines in a chiral reaction medium. Beilstein. J. Org. Chem. 2006, 2:18.
    • (2006) Beilstein. J. Org. Chem. , vol.2 , pp. 18
    • Pégot, B.1    Van Buu, O.N.2    Gori, D.3    Vo-Thanh, G.4
  • 44
    • 0032927941 scopus 로고    scopus 로고
    • Cancer multidrug resistance
    • Persidis A. Cancer multidrug resistance. Nat. Biotechnol. 1999, 17:94-95.
    • (1999) Nat. Biotechnol. , vol.17 , pp. 94-95
    • Persidis, A.1
  • 45
    • 70350714292 scopus 로고    scopus 로고
    • Preparation of 2-silicon-substituted 1,3-dienes and their Diels-Alder/cross-coupling reactions
    • Pidaparthi R.R., Junker C.S., Welker M.E., Day C.S., Wright M.W. Preparation of 2-silicon-substituted 1,3-dienes and their Diels-Alder/cross-coupling reactions. J. Org. Chem. 2009, 74:8290-8297.
    • (2009) J. Org. Chem. , vol.74 , pp. 8290-8297
    • Pidaparthi, R.R.1    Junker, C.S.2    Welker, M.E.3    Day, C.S.4    Wright, M.W.5
  • 46
    • 84871696693 scopus 로고
    • DNA topoisomerases and their inhibition by anthracyclines. In: Priebe, W. (Ed.), Anthracycline Antibiotics - New Analogues, Methods of Delivery and Mechanisms of Action. ACS Symposium Series 574, Washington, DC
    • Pommier, Y., 1995. DNA topoisomerases and their inhibition by anthracyclines. In: Priebe, W. (Ed.), Anthracycline Antibiotics - New Analogues, Methods of Delivery and Mechanisms of Action. ACS Symposium Series 574, Washington, DC, pp. 183-203.
    • (1995) , pp. 183-20
    • Pommier, Y.1
  • 47
    • 0032577901 scopus 로고    scopus 로고
    • Doxorubicin- and daunorubicin-glutathione conjugates, but not unconjugated drugs, competitively inhibit C4 transport mediated by MRP/GS-X Pump
    • Priebe W., Krawczyk M., Kuo T., Yamane Y., Savaraj N., Ishikawa T. Doxorubicin- and daunorubicin-glutathione conjugates, but not unconjugated drugs, competitively inhibit C4 transport mediated by MRP/GS-X Pump. Biochem. Biophys. Res. Commun. 1998, 247:859-863.
    • (1998) Biochem. Biophys. Res. Commun. , vol.247 , pp. 859-863
    • Priebe, W.1    Krawczyk, M.2    Kuo, T.3    Yamane, Y.4    Savaraj, N.5    Ishikawa, T.6
  • 48
    • 0030840016 scopus 로고    scopus 로고
    • Binding of two novel bisdaunorubicins to DNA studied by NMR spectroscopy
    • Robinson H., Priebe W., Chaires J.B., Wang A.H.-J. Binding of two novel bisdaunorubicins to DNA studied by NMR spectroscopy. Biochemistry 1997, 36:8663-8670.
    • (1997) Biochemistry , vol.36 , pp. 8663-8670
    • Robinson, H.1    Priebe, W.2    Chaires, J.B.3    Wang, A.H.-J.4
  • 49
    • 0009622204 scopus 로고
    • Computer-assisted mechanistic evaluation of organic reactions. 7. Six-electron cycloadditions
    • Schmidt J.A., Jorgensen W.L. Computer-assisted mechanistic evaluation of organic reactions. 7. Six-electron cycloadditions. J. Org. Chem. 1983, 48:3923-3941.
    • (1983) J. Org. Chem. , vol.48 , pp. 3923-3941
    • Schmidt, J.A.1    Jorgensen, W.L.2
  • 50
    • 0025987026 scopus 로고
    • Anthracycline immunoconjugates prepared by a site-specific linkage via an amino-dextran intermediate carrier
    • Shih L.B., Goldenburg D.M., Xuan H., Lu H., Sharkey R.M., Hall T.C. Anthracycline immunoconjugates prepared by a site-specific linkage via an amino-dextran intermediate carrier. Cancer Res. 1991, 51:4192-4198.
    • (1991) Cancer Res. , vol.51 , pp. 4192-4198
    • Shih, L.B.1    Goldenburg, D.M.2    Xuan, H.3    Lu, H.4    Sharkey, R.M.5    Hall, T.C.6
  • 51
    • 84871678004 scopus 로고    scopus 로고
    • SPARTAN'08, Version 1.2.0 Build 132. Wavefunction Inc., Irvine, CA, 2009
    • SPARTAN'08, 2009. Version 1.2.0 Build 132. Wavefunction Inc., Irvine, CA, 2009.
    • (2009)
  • 52
    • 79958276362 scopus 로고    scopus 로고
    • Monosaccharides as chiral auxiliaries and ligands for asymmetric synthesis
    • Springer, Berlin, O. Fraser-Reid, K. Tatsuta, J. Thiem (Eds.)
    • Tadano K., Totani K. Monosaccharides as chiral auxiliaries and ligands for asymmetric synthesis. Glycoscience 2008, 1029-1075. Springer, Berlin. O. Fraser-Reid, K. Tatsuta, J. Thiem (Eds.).
    • (2008) Glycoscience , pp. 1029-1075
    • Tadano, K.1    Totani, K.2
  • 53
    • 0008318185 scopus 로고
    • A short and efficient synthesis of 11-deoxyanthracyclinones: strong base-induced cycloaddition of the suitably substituted tetrahydrohomophthalic anhydride
    • Tamura Y., Sasho M., Ohe S., Akai S., Kita Y. A short and efficient synthesis of 11-deoxyanthracyclinones: strong base-induced cycloaddition of the suitably substituted tetrahydrohomophthalic anhydride. Tetrahedron Lett. 1985, 26:1549-1552.
    • (1985) Tetrahedron Lett. , vol.26 , pp. 1549-1552
    • Tamura, Y.1    Sasho, M.2    Ohe, S.3    Akai, S.4    Kita, Y.5
  • 54
    • 84871671906 scopus 로고    scopus 로고
    • Combinatorial synthesis of linearly condensed polycyclic compounds, including anthracyclinones, through tandem Diels-Alder additions
    • Springer, Berlin
    • Vogel P. Combinatorial synthesis of linearly condensed polycyclic compounds, including anthracyclinones, through tandem Diels-Alder additions. Topics in Current Chemistry: Anthracycline Chemistry and Biology I 2008, vol. 282:87-214. Springer, Berlin.
    • (2008) Topics in Current Chemistry: Anthracycline Chemistry and Biology I , vol.282 , pp. 87-214
    • Vogel, P.1
  • 56
    • 0030014783 scopus 로고    scopus 로고
    • DNA topoisomerases
    • Wang J.C. DNA topoisomerases. Annu. Rev. Biochem. 1996, 65:635-692.
    • (1996) Annu. Rev. Biochem. , vol.65 , pp. 635-692
    • Wang, J.C.1
  • 58
    • 0010700677 scopus 로고    scopus 로고
    • Asymmetric Diels-Alder reactions
    • Chapman & Hall, London, G.R. Stephenson (Ed.)
    • Whiting A. Asymmetric Diels-Alder reactions. Advanced Asymmetric Synthesis 1996, 126-145. Chapman & Hall, London. G.R. Stephenson (Ed.).
    • (1996) Advanced Asymmetric Synthesis , pp. 126-145
    • Whiting, A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.