SCOPUS 정보 검색 플랫폼

Volumn , Issue 12, 2008, Pages 1870-1876

Transition metals in organic synthesis, Part 87:1 An efficient palladium-catalyzed route to 2-oxygenated and 2,7-dioxygenated carbazole alkaloids - Total synthesis of 2-methoxy-3-methylcarbazole, glycosinine, clausine L, mukonidine, and clausine V

(5) Forke, Ronny a Krahl, Micha P a Däbritz, Frank a Jäger, Anne a Knölker, Hans Joachim a

a DRESDEN UNIVERSITY OF TECHNOLOGY (Germany)

Author keywords

Alkaloids; Antibiotics; Catalysis; Cyclizations; Palladium

Indexed keywords

2 METHOXY 3 METHYLCARBAZOLE; ALKALOID DERIVATIVE; CARBAZOLE DERIVATIVE; CLAUSINE L; CLAUSINE V; GLYCOSININE; ISOMUKONIDINE; MUKONIDINE; PALLADIUM; TRANSITION ELEMENT;

ARTICLE; CATALYSIS; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION; OXYGENATION;

EID: 48449103519 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1078508 Document Type: Article

Times cited : (73)

References (68)

1
- 48449086420
- Part 86: Forke, R.; Jäger, A.; Knölker, H.-J. Org. Biomol. Chem. 2008, 6, in press.
- Part 86: Forke, R.; Jäger, A.; Knölker, H.-J. Org. Biomol. Chem. 2008, 6, in press.

2
- 0025999191
- For some comprehensive reviews, see: a, Herz, W, Grisebach, H, Kirby, G. W, Steglich, W, Tamm, C, Eds, Springer: Wien
- For some comprehensive reviews, see: (a) Chakraborty, D. P.; Roy, S. In Progress in the Chemistry of Organic Natural Products, Vol. 57; Herz, W.; Grisebach, H.; Kirby, G. W.; Steglich, W.; Tamm, C., Eds.; Springer: Wien, 1991, 71.
- (1991) Progress in the Chemistry of Organic Natural Products , vol.57 , pp. 71
- Chakraborty, D.P.¹ Roy, S.²

3
- 77957036993
- Cordell, G. A, Ed, Academic Press: New York
- (b) Chakraborty, D. P. In The Alkaloids, Vol. 44; Cordell, G. A., Ed.; Academic Press: New York, 1993, 257.
- (1993) The Alkaloids , vol.44 , pp. 257
- Chakraborty, D.P.¹

4
- 0036826933
- (c) Knölker, H.-J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
- (2002) Chem. Rev , vol.102 , pp. 4303
- Knölker, H.-J.¹ Reddy, K.R.²

5
- 24644485154
- (d) Knölker, H.-J. Top. Curr. Chem. 2005, 244, 115.
- (2005) Top. Curr. Chem , vol.244 , pp. 115
- Knölker, H.-J.¹

6
- 44949230366
- Cordell, G. A, Ed, Academic Press: Amsterdam
- (e) Knölker, H.-J.; Reddy, K. R. In The Alkaloids, Vol. 65; Cordell, G. A., Ed.; Academic Press: Amsterdam, 2008, 1.
- (2008) The Alkaloids , vol.65 , pp. 1
- Knölker, H.-J.¹ Reddy, K.R.²

7
- 0001618706
- For accounts, see: a
- For accounts, see: (a) Pindur, U. Chimia 1990, 44, 406.
- (1990) Chimia , vol.44 , pp. 406
- Pindur, U.¹

8
- 0001245957
- (b) Bergman, J.; Pelcman, B. Pure Appl. Chem. 1990, 62, 1967.
- (1990) Pure Appl. Chem , vol.62 , pp. 1967
- Bergman, J.¹ Pelcman, B.²

9
- 0000335348
- Chem. Soc
- (c) Kawasaki, T.; Sakamoto, M. J. Indian Chem. Soc. 1994, 71, 443.
- (1994) Indian , vol.71 , pp. 443
- Kawasaki, T.¹ Sakamoto, M.J.²

10
- 0002551272
- (d) Moody, C. J. Synlett 1994, 681.
- (1994) Synlett , pp. 681
- Moody, C.J.¹

11
- 48449106786
- Hibino, S.; Sugino, E. In Advances in Nitrogen Heterocycles, 1; Moody, C. J., Ed.; JAI Press: Greenwich CT, 1995, 205.
- (e) Hibino, S.; Sugino, E. In Advances in Nitrogen Heterocycles, Vol. 1; Moody, C. J., Ed.; JAI Press: Greenwich CT, 1995, 205.

12
- 0035008894
- (f) Kirsch, G. H. Curr. Org. Chem. 2001, 5, 507.
- (2001) Curr. Org. Chem , vol.5 , pp. 507
- Kirsch, G.H.¹

13
- 27744529130
- (g) Lemster, T.; Pindur, U. Recent Res. Dev. Org. Bioorg. Chem. 2002, 5, 99.
- (2002) Recent Res. Dev. Org. Bioorg. Chem , vol.5 , pp. 99
- Lemster, T.¹ Pindur, U.²

14
- 10844277538
- (h) Knölker, H.-J. Curr. Org. Synth. 2004, 1, 309.
- (2004) Curr. Org. Synth , vol.1 , pp. 309
- Knölker, H.-J.¹

15
- 7044235100
- (i) Fröhner, W.; Krahl, M. P.; Reddy, K. R.; Knölker, H.-J. Heterocycles 2004, 63, 2393.
- (2004) Heterocycles , vol.63 , pp. 2393
- Fröhner, W.¹ Krahl, M.P.² Reddy, K.R.³ Knölker, H.-J.⁴

16
- 33745683898
- Recent contributions: (a) Yamabuki, A.; Fujinawa, H.; Choshi, T.; Tohyama, S.; Matsumoto, K.; Ohmura, K.; Nobuhiro, J.; Hibino, S. Tetrahedron Lett. 2006, 47, 5859.
- Recent contributions: (a) Yamabuki, A.; Fujinawa, H.; Choshi, T.; Tohyama, S.; Matsumoto, K.; Ohmura, K.; Nobuhiro, J.; Hibino, S. Tetrahedron Lett. 2006, 47, 5859.

17
- 33845585332
- (b) Bedford, R. B.; Betham, M. J. Org. Chem. 2006, 71, 9403.
- (2006) J. Org. Chem , vol.71 , pp. 9403
- Bedford, R.B.¹ Betham, M.²

18
- 33947158483
- (c) Yamamoto, M.; Matsubara, S. Chem. Lett. 2007, 36, 172.
- (2007) Chem. Lett , vol.36 , pp. 172
- Yamamoto, M.¹ Matsubara, S.²

19
- 33847015242
- (d) Forke, R.; Krahl, M. P.; Krause, T.; Schlechtingen, G.; Knölker, H.-J. Synlett 2007, 268.
- (2007) Synlett , pp. 268
- Forke, R.¹ Krahl, M.P.² Krause, T.³ Schlechtingen, G.⁴ Knölker, H.-J.⁵

20
- 33751522598
- (e) Liu, Z.; Larock, R. C. Tetrahedron 2007, 63, 347.
- (2007) Tetrahedron , vol.63 , pp. 347
- Liu, Z.¹ Larock, R.C.²

21
- 34248204484
- (f) Ackermann, L.; Althammer, A. Angew. Chem. Int. Ed. 2007, 46, 1627.
- (2007) Angew. Chem. Int. Ed , vol.46 , pp. 1627
- Ackermann, L.¹ Althammer, A.²

22
- 34249306540
- (g) Lebold, T. P.; Kerr, M. A. Org. Lett. 2007, 9, 1883.
- (2007) Org. Lett , vol.9 , pp. 1883
- Lebold, T.P.¹ Kerr, M.A.²

23
- 35748974155
- (h) Watanabe, T.; Ueda, S.; Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. Chem. Commun. 2007, 4516.
- (2007) Chem. Commun , pp. 4516
- Watanabe, T.¹ Ueda, S.² Inuki, S.³ Oishi, S.⁴ Fujii, N.⁵ Ohno, H.⁶

24
- 36348956240
- (i) St. Jean Jr., D. J.; Poon, S. F.; Schwarzbach, J. L. Org. Lett. 2007, 9, 4893.
- (2007) Org. Lett , vol.9 , pp. 4893
- St. Jean Jr., D.J.¹ Poon, S.F.² Schwarzbach, J.L.³

25
- 34548749746
- (j) Liu, C.-Y.; Knöchel, P. J. Org. Chem. 2007, 72, 7106.
- (2007) J. Org. Chem , vol.72 , pp. 7106
- Liu, C.-Y.¹ Knöchel, P.²

26
- 37149028848
- (k) Naffziger, M. R.; Ashburn, B. O.; Perkins, J. R.; Carter, R. G. J. Org. Chem. 2007, 72, 9857.
- (2007) J. Org. Chem , vol.72 , pp. 9857
- Naffziger, M.R.¹ Ashburn, B.O.² Perkins, J.R.³ Carter, R.G.⁴

27
- 0011977605
- Bhattacharyya, P.; Jash, S. S.; Chowdhury, B. K. Chem. Ind. (London) 1986, 246.
- (1986) Chem. Ind. (London) , pp. 246
- Bhattacharyya, P.¹ Jash, S.S.² Chowdhury, B.K.³

28
- 0001124057
- Bhattacharyya, P.; Chakraborty, A. Phytochemistry 1984, 23, 471.
- (1984) Phytochemistry , vol.23 , pp. 471
- Bhattacharyya, P.¹ Chakraborty, A.²

29
- 0011919243
- Chakraborty, D. P.; Roy, S.; Guha, R. J. Indian Chem. Soc. 1978, 55, 1114.
- (1978) J. Indian Chem. Soc , vol.55 , pp. 1114
- Chakraborty, D.P.¹ Roy, S.² Guha, R.³

30
- 0001307645
- Wu, T.-S.; Huang, S.-C.; Lai, J.-S.; Teng, C.-M.; Ko, F.-N.; Kuoh, C.-S. Phytochemistry 1993, 32, 449.
- (1993) Phytochemistry , vol.32 , pp. 449
- Wu, T.-S.¹ Huang, S.-C.² Lai, J.-S.³ Teng, C.-M.⁴ Ko, F.-N.⁵ Kuoh, C.-S.⁶

31
- 0028139593
- Bhattacharyya, P.; Maiti, A. K.; Basu, K.; Chowdhury, B. K. Phytochemistry 1994, 35, 1085.
- (1994) Phytochemistry , vol.35 , pp. 1085
- Bhattacharyya, P.¹ Maiti, A.K.² Basu, K.³ Chowdhury, B.K.⁴

32
- 0011987041
- Bhagwanth, M. R. R.; Rama Rao, A. V.; Venkataraman, K. Indian J. Chem. 1969, 7, 1065.
- (1969) Indian J. Chem , vol.7 , pp. 1065
- Bhagwanth, M.R.R.¹ Rama Rao, A.V.² Venkataraman, K.³

33
- 0011975106
- Bhattacharyya, P.; Chowdhury, B. K. Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem. 1985, 24, 452.
- (1985) Indian J. Chem., Sect. B: Org. Chem. Incl. Med. Chem , vol.24 , pp. 452
- Bhattacharyya, P.¹ Chowdhury, B.K.²

34
- 0025036617
- Ruangrungsi, N.; Ariyaprayoon, J.; Lange, G. L.; Organ, M. G. J. Nat. Prod. 1990, 53, 946.
- (1990) J. Nat. Prod , vol.53 , pp. 946
- Ruangrungsi, N.¹ Ariyaprayoon, J.² Lange, G.L.³ Organ, M.G.⁴

35
- 0000295608
- Jash, S. S.; Biswas, G. K.; Bhattacharyya, S. K.; Bhattacharyya, P.; Chakraborty, A.; Chowdhury, B. K. Phytochemistry 1992, 31, 2503.
- (1992) Phytochemistry , vol.31 , pp. 2503
- Jash, S.S.¹ Biswas, G.K.² Bhattacharyya, S.K.³ Bhattacharyya, P.⁴ Chakraborty, A.⁵ Chowdhury, B.K.⁶

36
- 0024238407
- Chaichantipyth, C.; Pummangura, S.; Naowsaran, K.; Thanyavuthi, D.; Anderson, J. E.; McLaughlin, J. L. J. Nat. Prod. 1988, 51, 1285.
- (1988) J. Nat. Prod , vol.51 , pp. 1285
- Chaichantipyth, C.¹ Pummangura, S.² Naowsaran, K.³ Thanyavuthi, D.⁴ Anderson, J.E.⁵ McLaughlin, J.L.⁶

37
- 0032833109
- Wu, T.-S.; Huang, S.-C.; Wu, P.-L.; Kuoh, C.-S. Phytochemistry 1999, 52, 523.
- (1999) Phytochemistry , vol.52 , pp. 523
- Wu, T.-S.¹ Huang, S.-C.² Wu, P.-L.³ Kuoh, C.-S.⁴

38
- 0001169986
- Knölker, H.-J.; Bauermeister, M. J. Indian Chem. Soc. 1994, 71, 345.
- (1994) J. Indian Chem. Soc , vol.71 , pp. 345
- Knölker, H.-J.¹ Bauermeister, M.²

39
- 0041994637
- Knölker, H.-J.; Goesmann, H.; Hofmann, C. Synlett 1996, 737.
- (1996) Synlett , pp. 737
- Knölker, H.-J.¹ Goesmann, H.² Hofmann, C.³

40
- 0031013248
- (a) Knölker, H.-J.; Wolpert, M. Tetrahedron Lett. 1997, 38, 533.
- (1997) Tetrahedron Lett , vol.38 , pp. 533
- Knölker, H.-J.¹ Wolpert, M.²

41
- 0042532270
- (b) Knölker, H.-J.; Wolpert, M. Tetrahedron 2003, 59, 5317.
- (2003) Tetrahedron , vol.59 , pp. 5317
- Knölker, H.-J.¹ Wolpert, M.²

42
- 25444506614
- Kataeva, O.; Krahl, M. P.; Knölker, H.-J. Org. Biomol. Chem. 2005, 3, 3099.
- (2005) Org. Biomol. Chem , vol.3 , pp. 3099
- Kataeva, O.¹ Krahl, M.P.² Knölker, H.-J.³

43
- 33747876110
- Krahl, M. P.; Jäger, A.; Krause, T.; Knölker, H.-J. Org. Biomol. Chem. 2006, 4, 3215.
- (2006) Org. Biomol. Chem , vol.4 , pp. 3215
- Krahl, M.P.¹ Jäger, A.² Krause, T.³ Knölker, H.-J.⁴

44
- 0032541260
- (a) Hartwig, J. F. Angew. Chem. Int. Ed. 1998, 37, 2046.
- (1998) Angew. Chem. Int. Ed , vol.37 , pp. 2046
- Hartwig, J.F.¹

45
- 0000157513
- (b) Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131.
- (2002) Top. Curr. Chem , vol.219 , pp. 131
- Muci, A.R.¹ Buchwald, S.L.²

46
- 33847801634
- (a) Åkermark, B.; Eberson, L.; Jonsson, E.; Pettersson, E. J. Org. Chem. 1975, 40, 1365.
- (1975) J. Org. Chem , vol.40 , pp. 1365
- Åkermark, B.¹ Eberson, L.² Jonsson, E.³ Pettersson, E.⁴

47
- 0019165813
- (b) Miller, R. B.; Moock, T. Tetrahedron Lett. 1980, 21, 3319.
- (1980) Tetrahedron Lett , vol.21 , pp. 3319
- Miller, R.B.¹ Moock, T.²

48
- 85004464969
- (c) Furukawa, H.; Ito, C.; Yogo, M.; Wu, T.-S. Chem. Pharm. Bull. 1986, 34, 2672.
- (1986) Chem. Pharm. Bull , vol.34 , pp. 2672
- Furukawa, H.¹ Ito, C.² Yogo, M.³ Wu, T.-S.⁴

49
- 0028136733
- (d) Knölker, H.-J.; O'Sullivan, N. Tetrahedron 1994, 50, 10893.
- (1994) Tetrahedron , vol.50 , pp. 10893
- Knölker, H.-J.¹ O'Sullivan, N.²

50
- 0036199694
- (e) Knölker, H.-J.; Fröhner, W.; Reddy, K. R. Synthesis 2002, 557.
- (2002) Synthesis , pp. 557
- Knölker, H.-J.¹ Fröhner, W.² Reddy, K.R.³

51
- 0038372599
- (f) Knölker, H.-J.; Reddy, K. R. Heterocycles 2003, 60, 1049.
- (2003) Heterocycles , vol.60 , pp. 1049
- Knölker, H.-J.¹ Reddy, K.R.²

52
- 3843065849
- (g) Knölker, H.-J.; Knöll, J. Chem. Commun. 2003, 1170.
- (2003) Chem. Commun , pp. 1170
- Knölker, H.-J.¹ Knöll, J.²

53
- 48449095124
- Characteristic Spectroscopic Data of the 2-Oxygenated and 2,7-Dioxygenated Carbazole Alkaloids 2-Methoxy-3-methylcarbazole (4) Colorless crystals; mp 221°C (lit.11 223°C, UV (MeOH, λmax, 230, 237, 257, 264 (sh, 301, 331 um. IR (ATR, ν, 3402, 2992, 2919, 2851, 1631, 1609, 1496, 1455, 1340, 1304, 1230, 1194, 1175, 1139, 1109, 1038, 1014, 1003, 885, 819, 766, 749, 725 cm-1. 1H NMR (500 MHz, acetone-d6, δ, 2.32 (s, 3 H, 3.89 (s, 3 H, 7.02 (s, 1 H, 7.12 (t, J, 7.8 Hz, 1 H, 7.27 (t, J, 7.8 Hz, 1 H, 7.43 (d, J, 7.8 Hz, 1 H, 7.82 (s, 1 H, 7.97 (d, J, 7.8 Hz, 1 H, 10.05 (br s, 1 H, 13C NMR and DEPT (125 MHz, acetone-d6, δ, 16.87 (CH3, 55.68 (CH3, 93.35 (CH, 111.27 (CH, 116.73 (C, 118.95 (C, 119.43 (CH, 119.79 (CH, 121.94 (CH, 124.14 (C, 124.60 (CH, 140.61 (C, 140.74 (C, 158.20 C, MS
- 6)

54
- 33845938814
- Lafrance, M.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 16496.
- (2006) J. Am. Chem. Soc , vol.128 , pp. 16496
- Lafrance, M.¹ Fagnou, K.²

55
- 48449086419
- Crystal Data for Glycosinine (5) C14H 11NO2, crystal size: 0.34 x 0.21 x 0.09 mm3, M, 225.24 g mol-1, monoclinic, space group: P2 1/c, λ, 0.71073 Å, a, 11.235 (1, b, 13.717 (1, c, 7.259 (2) Å, β, 106.38 (1)°, V, 1073.3 (3) Å3, Z, 4, D calcd, 1.394 g cm-3, μ, 0.094 mm-1, T, 198 (2) K, θ range, 3.28-30.00°; reflections collected: 26896, independent: 3108 (Rint, 0.0999, 159 parameters. The structure was solved by direct methods and refined by full-matrix least-squares on F2; final R indices [I > 2σI, R1, 0.0514, wR2, 0.1018; maximal residual electron density: 0.273 e Å-3. CCDC-686500 contains the supplementary crystallographic data for this pa
- -3. CCDC-686500 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.uk/data_request/cif.

56
- 48449093699
- Manganese dioxide (precipitated, active) from Merck (art. 805958).
- (a) Manganese dioxide (precipitated, active) from Merck (art. 805958).

57
- 19644397969
- (b) Corey, E. J.; Gilman, N. W.; Ganem, B. E. J. Am. Chem. Soc. 1968, 90, 5616.
- (1968) J. Am. Chem. Soc , vol.90 , pp. 5616
- Corey, E.J.¹ Gilman, N.W.² Ganem, B.E.³

58
- 84986947049
- (c) Knölker, H.-J. J. Prakt. Chem. 1995, 337, 75.
- (1995) J. Prakt. Chem , vol.337 , pp. 75
- Knölker, H.-J.¹

59
- 48449104299
- Crystal Data for Isomukonidine (13) C14H 11NO3, crystal size: 0.32 x 0.29 x 0.28 mm3, M, 241.24 g mol-1, monoclinic, space group: C2/c, λ, 0.71073 Å, a, 16.423 (3, b, 7.5231 (15, c, 18.548 (4) Å, β, 96.25 (3)°, V, 2278.1 (8) Å3, Z, 8, Dcalcd, 1.407 g cm-3, μ, 0.100 mm-1, T, 298 (2) K, θ range, 3.13-30.02°; reflections collected: 34016, independent: 3328 (Rint, 0.0590, 168 parameters. The structure was solved by direct methods and refined by full-matrix least-squares on F2; final R indices [I > 2σI, R1, 0.0430, wR2, 0.1125; maximal residual electron density: 0.316 e Å-3. CCDC-686501 contains the supplementary crystallographic data for this paper. Thes
- -3. CCDC-686501 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.uk/data_request/cif.

60
- 33749347309
- Sridharan, V.; Martin, M. A.; Menéndez, J. C. Synlett 2006, 2375.
- (2006) Synlett , pp. 2375
- Sridharan, V.¹ Martin, M.A.² Menéndez, J.C.³

61
- 48449083047
- Experimental Procedure for the Microwave-Assisted Palladium(II, Catalyzed Oxidative Cyclization The diarylamine 16 (400 mg, 1.01 mmol, Pd(OAc)2 (46.3 mg, 0.21 mmol, Cu(OAc)2 (458 mg, 2.52 mmol, and pivalic acid (4.7 g) were heated in a 10 mL microwave vessel for 2 h at 130°C. The reaction mixture was extracted with a sat. solution of K2CO3 until the aqueous layer showed no further blue color. The aqueous layer was extracted with Et2O and the combined organic layers were dried with MgSO4. Removal of the solvent in vacuum and flash chromatography (PE-Et2O, gradient elution from 4:1 to 1:1) of the crude product on SiO2 provided 3-cyano-7- triisopropylsilyloxy-4-methoxycarbazole (18, yield 17.0 mg, 4, as colorless crystals (mp 141-143°C, then the diarylamine 16 yield 28.2 mg, 7, as colorless crystals, and, as the most polar fraction, 3-cyano-7-triisopropylsil
- 2 provided 3-cyano-7- triisopropylsilyloxy-4-methoxycarbazole (18) (yield 17.0 mg, 4%) as colorless crystals (mp 141-143°C), then the diarylamine 16 (yield 28.2 mg, 7%) as colorless crystals, and, as the most polar fraction, 3-cyano-7-triisopropylsilyloxy-2-methoxycarbazole (17) (yield 266.0 mg, 67%) as colorless crystals (mp 180-181°C).

62
- 0003686469
- Olah, G. A.; Narang, S. C.; Gupta, B. G. B.; Malhotra, R. J. Org. Chem. 1979, 44, 1247.
- (1979) J. Org. Chem , vol.44 , pp. 1247
- Olah, G.A.¹ Narang, S.C.² Gupta, B.G.B.³ Malhotra, R.⁴

63
- 84990107462
- Bhatt, M. V.; Kulkarni, S. U. Synthesis 1983, 249.
- (1983) Synthesis , pp. 249
- Bhatt, M.V.¹ Kulkarni, S.U.²

64
- 85065604717
- Winterfeldt, E. Synthesis 1975, 617.
- (1975) Synthesis , pp. 617
- Winterfeldt, E.¹

65
- 0001144773
- For a previous synthesis, see
- For a previous synthesis, see: Hsieh, B. R.; Litt, M. H. Macromolecules 1985, 18, 1388.
- (1985) Macromolecules , vol.18 , pp. 1388
- Hsieh, B.R.¹ Litt, M.H.²

66
- 33748641380
- (a) Choi, T. A.; Czerwonka, R.; Fröhner, W.; Krahl, M. P.; Reddy, K. R.; Franzblau, S. G.; Knölker, H.-J. ChemMedChem 2006, 1, 812.
- (2006) ChemMedChem , vol.1 , pp. 812
- Choi, T.A.¹ Czerwonka, R.² Fröhner, W.³ Krahl, M.P.⁴ Reddy, K.R.⁵ Franzblau, S.G.⁶ Knölker, H.-J.⁷

67
- 38549085748
- (b) Choi, T. A.; Czerwonka, R.; Knöll, J.; Krahl, M. P.; Reddy, K. R.; Franzblau, S. G.; Knölker, H.-J. Med. Chem. Res. 2006, 15, 28.
- (2006) Med. Chem. Res , vol.15 , pp. 28
- Choi, T.A.¹ Czerwonka, R.² Knöll, J.³ Krahl, M.P.⁴ Reddy, K.R.⁵ Franzblau, S.G.⁶ Knölker, H.-J.⁷

68
- 52949128403
- DOI: 10.1007/s00044-007- 9073-0
- (c) Choi, T. A.; Czerwonka, R.; Forke, R.; Jäger, A.; Knöll, J.; Krahl, M. P.; Krause, T.; Reddy, K. R.; Franzblau, S. G.; Knölker, H.-J. Med. Chem. Res. 2008, 17, DOI: 10.1007/s00044-007- 9073-0.
- (2008) Med. Chem. Res , vol.17
- Choi, T.A.¹ Czerwonka, R.² Forke, R.³ Jäger, A.⁴ Knöll, J.⁵ Krahl, M.P.⁶ Krause, T.⁷ Reddy, K.R.⁸ Franzblau, S.G.⁹ Knölker, H.-J.¹⁰

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.