SCOPUS 정보 검색 플랫폼

Journal of the American Chemical Society

Volumn 123, Issue 22, 2001, Pages 5249-5259

Insights into long-range structural effects on the stereochemistry of aldol condensations: A practical total synthesis of desoxyepothilone F

(8) Chul Bom Lee, a Wu, Z b Zhang, F b Chappell, M D a Stachel, S J a Chou, T C a Guan, Y a Danishefsky, S J a,b

a MEMORIAL SLOAN KETTERING CANCER CENTER (United States)

b Och Spine at New York Presbyterian Hospitals (United States)

Author keywords

[No Author keywords available]

Indexed keywords

KETO FUNCTIONS;

REDUCTION; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CONDENSATION;

21 HYDROXY 12,13 DESOXYEPOTHILONE B; 21 HYDROXYEPOTHILONE D; ANTINEOPLASTIC AGENT; CARBON; DESOXYEPOTHILONE F; EPOTHILONE DERIVATIVE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ANALYTIC METHOD; ARTICLE; CHIRALITY; COVALENT BOND; DRUG SYNTHESIS; MOLECULAR INTERACTION; POLYMERIZATION; REACTION ANALYSIS; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS;

ANTINEOPLASTIC AGENTS; EPOTHILONES; LACTONES; STEREOISOMERISM; THIAZOLES;

EID: 0034814540 PISSN: 00027863 EISSN: None Source Type: Journal
DOI: 10.1021/ja010039j Document Type: Article

Times cited : (74)

References (106)

1
- 0003671040
- American Chemical Society: San Diego
- (1995) Taxane Anticancer Agent
- Georg, G.I.¹ Chen, T.T.² Ojima, I.³ Vyas, D.M.⁴

2
- 0003897919
- Elsevier: New York
- (1995) The Chemistry and Pharmacology of Taxol and its Derivatives
- Farin, V.¹

3
- 0003469887
- CRC Press: Boca Raton, FL
- (1995) Taxol: Sciences & Applications
- Suffness, M.¹

4
- 0004112137
- Wiley-Liss: New York
- (1993) Microtubules
- Hyams, J.F.¹ Loyd, C.W.²

5
- 0000467248
- (1979) Nature , vol.277 , pp. 665
- Horwitz, S.B.¹ Fant, J.² Schiff, P.B.³

6
- 0025160288
- (1990) J. Org. Chem. , vol.55 , pp. 4912
- Gunasakera, S.P.¹ Gunasakera, M.² Longley, R.E.³ Schulte, G.K.⁴

7
- 0030984058
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 8744
- Lindel, T.¹ Jensen, P.R.² Fenical, W.³ Long, B.H.⁴ Casazza, A.M.⁵ Carboni, J.⁶ Fairchild, C.R.⁷

8
- 0033083045
- (1999) Cancer Res. , vol.59 , pp. 653
- Moobery, S.L.¹ Tien, G.² Hernandez, A.H.³ Pluburukarn, A.⁴ Davidson, B.S.⁵

9
- 0029776766
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1567
- Höfle, G.H.¹ Bedorf, N.² Steinmetz, H.³ Schomburg, D.⁴ Gerth, K.⁵ Reichenbach, H.⁶

10
- 0030018666
- (1996) J. Antibiot. , vol.49 , pp. 560
- Gerth, K.¹ Bedorf, N.² Höfle, G.H.³ Irsehik, H.⁴ Reichenbach, H.⁵

11
- 0027228024
- (1993) Semin. Oncol. , vol.20 , pp. 1
- Rowinsky, E.K.¹ Eisenhauer, E.A.² Chaudhry, V.³ Arbuck, S.G.⁴ Donehawer, R.C.⁵

12
- 0026702494
- (1992) J. Biol. Chem. , vol.267 , pp. 4338
- Fletcher, B.S.¹ Kujubadu, D.A.² Perrin, D.M.³ Herschman, H.R.⁴

13
- 0028803728
- (1995) Cell , vol.3 , pp. 493
- Tsuji, M.¹ Dubois, R.N.²

14
- 0030039047
- (1996) J. Allergy Clin. Immunol. , vol.97 , pp. 42
- Essayan, D.M.¹ Kagey-Sobotka, A.² Colarusso, P.J.³ Lichtenstein, L.M.⁴ Ozols, R.F.⁵ King, E.D.⁶

15
- 0030758777
- and references therein
- (1997) J. Biol. Chem. , vol.272 , pp. 17118
- Giannakakou, P.¹ Sackett, D.L.² Kang, Y.-K.³ Zhan, Z.⁴ Buters, J.T.⁵ Fojo, T.⁶ Poruchynsky, M.S.⁷

16
- 0029049468
- (1995) Cancer Res. , vol.55 , pp. 2325
- Bollag, D.M.¹ McQueney, P.A.² Zhu, J.³ Hensens, O.⁴ Koupal, L.⁵ Liesch, J.⁶ Goetz, M.⁷ Lazarides, E.⁸ Woods, C.M.⁹

17
- 0000429459
- (1995) Mol. Biol. Cell , vol.6 , pp. 2137
- Kowalski, R.J.¹ Terhaar, E.² Longley, R.E.³ Gunasekera, S.P.⁴ Lin, C.M.⁵ Day, B.V.⁶ Hamel, E.⁷

18
- 0034723333
- (2000) Science , vol.287 , pp. 640
- Tang, L.¹ Shah, S.² Chung, L.³ Carney, J.⁴ Katz, L.⁵ Khosla, C.⁶ Julien, B.⁷

19
- 0034141305
- (2000) Chem. Biol. , vol.7 , pp. 97
- Molnar, I.¹ Schupp, T.² Ono, M.³ Zirkle, R.E.⁴ Milnamow, M.⁵ Nowak-Thompson, B.⁶ Engel, N.⁷ Toupet, C.⁸ Stratmann, A.⁹ Cyr, D.D.¹⁰ Gorlach, J.¹¹ Mayo, J.M.¹² Hu, A.¹³ Goff, S.¹⁴ Schmid, J.¹⁵ Ligon, J.M.¹⁶

20
- 0034673927
- (2000) Gene , vol.249 , pp. 153
- Julien, B.¹ Shah, S.² Ziermann, R.³ Goldman, R.⁴ Katz, L.⁵ Khosla, C.⁶

21
- 0030850057
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 166
- Yang, Z.¹ He, Y.² Vourloumis, D.³ Vallberg, H.⁴ Nicolaou, K.C.⁵

22
- 0030980104
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 525
- Nicolaou, K.C.¹ Sarabia, F.² Ninkovic, S.³ Yang, Z.⁴

23
- 0030755282
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 7960
- Nicolaou, K.C.¹ He, Y.² Vourloumis, D.³ Vallberg, H.⁴ Roschangar, F.⁵ Sarabia, F.⁶ Ninkovic, S.⁷ Yang, Z.⁸ Trujillo, J.I.⁹

24
- 17744405184
- (1997) Nature , vol.387 , pp. 268
- Nicolaou, K.C.¹ Winssinger, N.² Pastor, J.³ Ninkovic, S.⁴ Sarabia, F.⁵ He, Y.⁶ Vourloumis, D.⁷ Yang, Z.⁸ Li, T.⁹ Giannakakou, P.¹⁰ Hamel, E.¹¹

25
- 0031881549
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 84
- Nicolaou, K.C.¹ He, Y.² Roschangar, F.³ King, N.P.⁴ Vourloumis, D.⁵ Li, T.H.⁶

26
- 0030894922
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 523
- Schinzer, D.¹ Limberg, A.² Bauer, A.³ Bohm, O.M.⁴ Cordes, M.⁵

27
- 0032869834
- (1999) Chem. Eur. J. , vol.5 , pp. 2483
- Schinzer, D.¹ Bauer, A.² Bohm, O.M.³ Limberg, A.⁴ Cordes, M.⁵

28
- 0032844073
- (1999) Chem. Eur. J , vol.5 , pp. 2492
- Schinzer, D.¹ Bauer, A.² Schieber, J.³

29
- 0032493824
- (1998) Chem. Commun. , pp. 1597
- May, S.A.¹ Grieco, P.A.²

30
- 0034598534
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 209
- Sawada, D.¹ Shibasaki, M.²

31
- 0034327638
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 10521
- Sawada, D.¹ Kanai, M.² Shibasaki, M.³

32
- 0034603098
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 581
- Martin, H.M.¹ Drescher, M.² Mulzer, J.³

33
- 0033525108
- (1999) J. Org. Chem. , vol.64 , pp. 684
- White, J.D.¹ Carter, R.G.² Sundermann, K.F.³

34
- 0033523815
- (1999) Org. Lett. , vol.1 , pp. 1431
- White, J.D.¹ Sundermann, K.F.² Carter, R.G.³

35
- 0034710515
- (2000) Org. Lett. , vol.2 , pp. 2575
- Zhu, B.¹ Panek, J.S.²

36
- 0030514018
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 2801
- Balog, A.¹ Meng, D.F.² Kamenecka, T.³ Bertinato, P.⁴ Su, D.S.⁵ Sorensen, E.J.⁶ Danishefsky, S.J.⁷

37
- 0030792331
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 757
- Su, D.-S.¹ Meng, D.F.² Bertinato, P.³ Balog, A.⁴ Sorensen, E.J.⁵ Danishefsky, S.J.⁶ Zheng, Y.H.⁷ Chou, T.C.⁸ He, L.F.⁹ Horwitz, S.B.¹⁰

38
- 0030669587
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 10073
- Meng, D.F.¹ Bertinato, P.² Balog, A.³ Su, D.S.⁴ Kamenecka, T.⁵ Sorensen, E.J.⁶ Danishefsky, S.J.⁷

39
- 0032538477
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2675
- Balog, A.¹ Harris, C.R.² Savin, K.³ Zhang, X.G.⁴ Chou, T.-C.⁵ Danishefsky, S.J.⁶

40
- 0033523260
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 7050
- Harris, C.R.¹ Kuduk, S.D.² Balog, A.³ Savin, K.⁴ Glunz, P.W.⁵ Danishefsky, S.J.⁶

41
- 0030808795
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2093
- Su, D.-S.¹ Balog, A.² Meng, D.³ Bertinato, P.⁴ Danishefsky, S.J.⁵ Zheng, Y.-H.⁶ Chou, T.-C.⁷ He, L.⁸ Horwitz, S.B.⁹

42
- 0032541259
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2014
- Nicolaou, K.C.¹ Roschangar, F.² Vourloumis, D.³

43
- 0032416734
- (1998) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 15798
- Chou, T.C.¹ Zhang, X.G.² Harris, C.R.³ Kuduk, S.D.⁴ Balog, A.⁵ Savin, K.A.⁶ Bertino, J.R.⁷ Danishefsky, S.J.⁸

44
- 0032483019
- (1998) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 9642
- Chou, T.C.¹ Zhang, X.G.² Balog, A.³ Su, D.S.⁴ Meng, D.F.⁵ Savin, K.⁶ Bertino, J.R.⁷ Danishefsky, S.J.⁸

45
- 0033550167
- (1999) J. Org. Chem. , vol.64 , pp. 8434
- Harris, C.R.¹ Danishefsky, S.J.²

46
- 0003349936
- (GBF). WO-A 9822461, 1998
- (1998) Chem. Abstr. , vol.129 , pp. 5346
- Reichenbach, H.¹ Höfle² Gerth, K.³ Steinmetz, H.⁴

47
- 0003300061
- Walsdorff, J.-H., Ed.; GBF: Braunschweig
- (1997) GBF Annual Report
- Höfle, G.¹

48
- 0343486338
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 1971
- Höfle, G.¹ Glaser, N.² Kiffe, M.³ Hecht, H.J.⁴ Sasse, F.⁵ Reichenbach, H.⁶

49
- 0031881549
- (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 84
- Nicolaou, K.C.¹ He, Y.² Roschangar, F.³ King, N.P.⁴ Vourloumis, D.⁵ Li, T.⁶

50
- 0034604432
- (2000) Chem. Eur. J. , vol.6 , pp. 2783
- Nicolaou, K.C.¹ Hepworth, D.² King, N.P.³ Finlay, M.R.V.⁴ Scarpelli, R.⁵ Pereira, M.M.A.⁶ Bollbuck, B.⁷ Bigot, A.⁸ Werschkun, B.⁹ Winssinger, N.¹⁰

51
- 0001136501
- (2000) J. Org. Chem. , vol.65 , pp. 6525
- Lee, C.B.¹ Chou, T.C.² Zhang, X.G.³ Wang, Z.G.⁴ Kuduk, S.D.⁵ Chappell, M.D.⁶ Stachel, S.J.⁷ Danishefsky, S.J.⁸

52
- 0028222650
- (1994) Tetrahedron , vol.50 , pp. 4259
- Noyori, R.¹

53
- 33845282793
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 5856
- Noyori, R.¹ Ohkuma, T.² Kitamura, M.³

54
- 0001065963
- (1992) J. Org. Chem. , vol.57 , pp. 6689
- King, S.A.¹ Thompson, A.S.² King, A.O.³ Verhoeven, T.R.⁴

55
- 0025769026
- (1991) Tetrahedron Lett. , vol.32 , pp. 4227
- Taber, D.F.¹ Silverberg, L.J.²

56
- 0029802228
- (1996) J. Org. Chem. , vol.61 , pp. 7998
- Bertinato, P.¹ Sorensen, E.J.² Meng, D.F.³ Danishefsky, S.J.⁴

57
- 0034201169
- (2000) Org. Lett. , vol.2 , pp. 1633
- Chappell, M.D.¹ Stachel, S.J.² Lee, C.B.³ Danishefsky, S.J.⁴

58
- 0030894922
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 523
- Schinzer, D.¹ Limberg, A.² Bauer, A.³ Bohm, O.M.⁴ Cordes, M.⁵

59
- 0032869834
- (1999) Chem. Eur. J. , vol.5 , pp. 2483
- Schinzer, D.¹ Bauer, A.² Bohm, O.M.³ Limberg, A.⁴ Cordes, M.⁵

60
- 0032844073
- (1999) Chem. Eur. J. , vol.5 , pp. 2492
- Schinzer, D.¹ Bauer, A.² Schieber, J.³

61
- 0003298892
- (1999) Chem. Commun. , vol.519
- Nicolaou, K.C.¹ Hepworth, D.² Finlay, M.R.V.³ King, N.P.⁴ Werschkun, B.⁵ Bigot, A.⁶

62
- 0003429481
- Reference 12(1)

63
- 0034602349
- (2000) J. Org. Chem. , vol.65 , pp. 7456
- Mulzer, J.¹ Mantouliolis, A.² Öhler, E.³

64
- 0030590984
- (1996) Tetrahedron Lett. , vol.37 , pp. 9179
- Mulzer, J.¹ Montoulidids, A.²

65
- 0000627973
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 5225
- Satoh, Y.¹ Serizawa, H.² Hara, S.³ Suzuki, A.⁴

66
- 0001015191
- (1991) J. Org. Chem. , vol.56 , pp. 4585
- Sharpless, K.B.¹ Amberg, W.² Beller, M.³ Chen, H.⁴ Hartung, J.⁵ Kawanami, Y.⁶ Lubben, D.⁷ Manoury, E.⁸ Ogino, Y.⁹ Shibata, T.¹⁰ Ukita, T.¹¹

67
- 0141712450
- (1992) J. Org. Chem. , vol.57 , pp. 2768
- Sharpless, K.B.¹ Amberg, W.² Bennani, Y.L.³ Crispino, G.A.⁴ Hartung, J.⁵ Jeong, K.-S.⁶ Kwong, H.-L.⁷ Morikawa, K.⁸ Wang, Z.-M.⁹ Xu, D.¹⁰ Zhang, X.-L.¹¹

68
- 0000882040
- (1992) J. Org. Chem. , vol.57 , pp. 5067
- Hashiyama, T.¹ Morikawa, K.² Sharpless, K.B.³

69
- 0024818190
- (1989) Tetrahedron Lett. , vol.52 , pp. 7415
- Fattori, D.¹ De Guchtencere, E.² Vogel, P.³

70
- 0003297271
- (1982) Tetrahedron Lett. , vol.23 , pp. 3571
- Gras, J.-L.¹ Kong Win Chang, Y.-Y.² Bertrand, M.³

71
- 0001594845
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 4346
- Evans, D.A.¹ Morrissey, M.M.² Dorow, R.L.³

72
- 0000594896
- (2000) Tetrahedron Lett. , vol.41 , pp. 1793
- Jung, J.E.¹ Ho, H.² Kim, H.-D.³

73
- 0028891048
- (1995) Tetrahedron Lett. , vol.36 , pp. 175
- Paterson, I.¹ Bower, S.² McLeod, M.D.³

74
- 0000166356
- (1989) Tetrahedron , vol.45 , pp. 1501
- Cardillo, G.¹ Orena, M.² Romero, M.³ Sandr, S.⁴

75
- 0002427724
- (1984) Tetrahedron Lett. , vol.25 , pp. 39
- Kelly, T.R.¹ Arvanitis, A.²

76
- 0034644037
- (2000) Org. Lett. , vol.2 , pp. 2165
- Crimmins, M.T.¹ Emmmitte, K.A.² Katz, J.D.³

77
- 0025108083
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 7001
- Evans, D.A.¹ Kaldor, S.W.² Jones, T.K.³ Clardy, J.⁴ Stout, T.J.⁵

78
- 0021826616
- (1985) Tetrahedron Lett. , vol.26 , pp. 4239
- Cossío, F.P.¹ Palomo, C.²

79
- 27844466269
- (1981) Tetrahedron Lett. , vol.22 , pp. 3815
- Nahm, S.¹ Weinreb, S.M.²

80
- 84953502363
- (1982) Synth. Commun. , vol.12 , pp. 989
- Levin, J.I.¹ Turos, E.² Weinreb, S.M.³

81
- 0030850837
- (1997) J. Org. Chem. , vol.62 , pp. 3804
- Ciufolini, M.A.¹ Shen, Y.C.²

82
- 37049087291
- (1994) J. Chem. Soc., Perkin Trans 1 , pp. 1257
- Soai, K.¹ Takahashi, K.²

83
- 4244117250
- (1992) Chem. Rev. , vol.92 , pp. 833
- Soai, K.¹ Niwa, S.²

84
- 84990142381
- (1989) Angew. Chem., Int. Ed. Engl. , vol.28 , pp. 495
- Duthaler, R.O.¹ Herold, P.² Lottenbach, W.³ Oretle, K.⁴ Reidiker, M.⁵

85
- 33947085552
- (1973) J. Am. Chem. Soc. , vol.95 , pp. 512
- Dale, J.A.¹ Mosher, H.S.²

86
- 0001412908
- (1995) J. Org. Chem. , vol.60 , pp. 3013
- Luke, G.P.¹ Morris, J.²

87
- 0027383971
- (1993) Tetrahedron Lett. , vol.34 , pp. 6871
- Evans, D.A.¹ Calter, M.A.²

88
- 0012876697
- (1987) J. Org. Chem. , vol.52 , pp. 4681
- McCarthy, P.A.¹ Kageyama, M.²

89
- 33748468588
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 8215
- Evans, D.A.¹ Urpí, F.² Somers, T.C.³ Clark, J.S.⁴ Bilodeau, M.T.⁵

90
- 0033583269
- (1999) Tetrahedron Lett. , vol.40 , pp. 2267
- Harris, C.R.¹ Kuduk, S.D.² Balog, A.³ Savin, K.⁴ Danishefsky, S.J.⁵

91
- 0003298894
- Unpublished results in these laboratories
- Harris, C.R.¹ Kuduk, S.D.² Lee, C.B.³

92
- 0000631206
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 6965
- Martin, V.A.¹ Murray, D.H.² Pratt, N.E.³ Zhao, Y.-B.⁴ Albizati, K.F.⁵

93
- 33845557437
- (1981) J. Org. Chem. , vol.46 , pp. 2290
- Heathcock, C.H.¹ Pirrung, M.C.² Lampe, J.³ Buse, C.T.⁴ Young, S.D.⁵

94
- 0000485490
- (1981) Tetrahedron Lett. , vol.22 , pp. 425
- Frater, G.¹

95
- 84985560897
- (1981) Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 971
- Seebach, D.¹ Wasmuth, D.²

96
- 33845554892
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 1737
- Evans, D.A.¹ Ennis, M.D.² Mathre, D.J.³

97
- 0001487759
- (1985) Tetrahedron Lett. , vol.26 , pp. 3931
- Williard, P.¹ Salvino, J.M.²

98
- 0000784039
- (1991) J. Org. Chem. , vol.56 , pp. 4151
- Roush, W.R.¹

99
- 0034671490
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 4505
- Wu, Z.¹ Zhang, F.² Danishefsky, S.J.³

100
- 0041790924
- (1996) Tetrahedron Lett. , vol.37 , pp. 8585
- Paterson, I.¹ Gibson, K.R.² Oballa, R.M.³

101
- 0000271703
- (1997) J. Org. Chem. , vol.62 , pp. 788
- Evans, D.A.¹ Coleman, P.J.² Côté, B.³

102
- 33748645648
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 673
- Tanimoto, N.¹ Gerritz, S.W.² Sawabe, A.³ Takeshi, N.⁴ Filla, S.A.⁵ Masamune, S.⁶

103
- 0025827992
- Also see ref 20
- (1992) J. Med. Chem. , vol.34 , pp. 1176
- Swindell, C.S.¹ Krauss, N.E.² Horwitz, S.B.³ Ringel, I.⁴

104
- 0003349940
- Personal communication
- Horwitz, S.B.¹

105
- 0003298457
- In Press
- J. Org. Chem.
- Stachel, S.J.¹ Lee, C.² Bommann, W.G.³ Spassova, M.⁴ Chappell, M.D.⁵ Danishefsky, S.J.⁶ Chou, T.-C.⁷ Guan, Y.⁸

106
- 4243731154
- Manuscript submitted
- Proc. Nat. Acad. Sci. U.S.A.
- Chou, T.-C.¹ Guan, Y.² Zhang, X.-G.³ Stachel, S.J.⁴ Lee, C.⁵ Danishefsky, S.J.⁶

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.