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Journal of Organic Chemistry

Volumn 66, Issue 4, 2001, Pages 1297-1309

Total synthesis of the calphostins: Application of Fischer carbene complexes and thermodynamic control of atropisomers

(5) Merlic, C A a Aldrich, C C a Albaneze Walker, J a Saghatelian, A a Mammen, J a

a UNIVERSITY OF CALIFORNIA (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CALPHOSTIN A; CALPHOSTIN B; CALPHOSTIN C; CALPHOSTIN D; CARBENOID; PERYLENE; PROTEIN KINASE C INHIBITOR; QUINONE DERIVATIVE; TRIFLUOROACETIC ACID;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; DRUG SYNTHESIS; STRUCTURE ANALYSIS; THERMODYNAMICS;

HYDROCARBONS; ISOMERISM; METHANE; MOLECULAR STRUCTURE; NAPHTHALENES; SPECTRUM ANALYSIS; THERMODYNAMICS;

EID: 0035936772 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo0014663 Document Type: Article

Times cited : (55)

References (106)

1
- 0024530912
- (1989) J. Antibiot. , vol.42 , pp. 153-155
- Kobayashi, E.¹ Ando, K.² Nakano, H.³ Tamaoki, T.⁴

2
- 0024438833
- (1989) J. Antibiot. , vol.42 , pp. 1470-1474
- Kobayashi, E.¹ Ando, K.² Nakano, H.³ Iida, T.⁴ Ohno, H.⁵ Morimoto, M.⁶ Tamaoki, T.⁷

3
- 0024449505
- (1989) J. Antibiot. , vol.42 , pp. 1475-1481
- Iida, T.¹ Kobayashi, E.² Yoshida, M.³ Sano, H.⁴

4
- 0002817656
- (1987) Prog. Chem. Org. Nat. Prod. , vol.52 , pp. 1-71
- Weiss, U.¹ Nasini, G.²

5
- 0024550448
- (1989) Biochem. Biophys. Res. Commun. , vol.159 , pp. 548-553
- Kobayashi, E.¹ Nakano, H.² Morimoto, M.³ Tamaoki, T.⁴

6
- 0024565678
- (1989) Cancer , vol.63 , pp. 1892-1903
- Nishizuka, Y.¹

7
- 0005824636
- (1998) Angew. Chem., Int. Ed. Engl. , vol.37 , pp. 689-749
- Hinterding, K.¹ Alonso-Díaz, D.² Waldmann, H.³

8
- 0027536556
- (1993) Agents Actions , vol.38 , pp. 135-146
- Bradshaw, D.¹ Hill, C.H.² Nixon, J.S.³ Wilkinson, S.E.⁴

9
- 0032987224
- (1999) Pharmacol. Ther. , vol.82 , pp. 263-267
- Parker, P.J.¹

10
- 0033036759
- (1999) Pharmacol. Ther. , vol.82 , pp. 293-301
- Fabbro, D.¹ Buchdnger, E.² Wood, J.³ Mestan, J.⁴ Hofmann, F.⁵ Ferrari, S.⁶ Mett, H.⁷ O'Reilly, T.⁸ Meyer, T.⁹

11
- 0033025959
- (1999) Pharmacol. Ther. , vol.82 , pp. 437-449
- Cho-Chung, Y.S.¹

12
- 0028811653
- (1995) J. Biol. Chem. , vol.270 , pp. 28495-28498
- Newton, A.C.¹

13
- 0031786125
- (1998) Cell Signal , vol.10 , pp. 529-542
- Liu, W.S.¹ Heckman, C.A.²

14
- 0030762437
- (1997) FASEB , vol.11 , pp. 649-669
- Hofmann, J.¹

15
- 0030881680
- PKCγ as a mediator of neuropathic pain
- (1997) Science , vol.278 , pp. 279-283
- Malmberg, A.B.¹ Chen, C.² Tonegawa, S.³ Basbaum, A.I.⁴

16
- 13344293711
- PKCβ implicated in the vascular complication of diabetes
- (1996) Science , vol.272 , pp. 728-731
- Ishii, H.¹ Jirousek, M.R.² Koya, D.³ Takagi, C.⁴ Xia, P.⁵ Clermont, A.⁶ Bursell, S.-E.⁷ Kern, T.S.⁸ Ballas, L.M.⁹ Heath, W.F.¹⁰ Stramm, L.E.¹¹ Feener, E.P.¹² King, G.L.¹³

17
- 0031963427
- PKCα as a target for antisense cancer chemotherapy
- (1998) Anti-Cancer Drug Design , vol.13 , pp. 35-45
- Geiger, T.¹ Müller, M.² Dean, N.M.³ Fabbro, D.⁴

18
- 0032537972
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 9159-9167
- Irie, K.¹ Oie, K.² Nakahara, A.³ Yanai, Y.⁴ Ohigashi, H.⁵ Wender, P.A.⁶ Fukuda, H.⁷ Konishi, H.⁸ Kikkawa, U.⁹

19
- 0003959046
- Academic Press: San Diego
- (1995) The Protein Kinase Facts Book
- Hardie, G.¹ Hanks, S.²

20
- 0032554112
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 457-458
- Sodeoka, M.¹ Arai, M.A.² Adachi, K.³ Uotsu, K.⁴ Shibasaki, M.⁵

21
- 0032856040
- (1999) Urology , vol.54 , pp. 573-577
- Beck, T.P.¹ Kirsh, E.J.² Chmura, S.J.³ Kovar, D.A.⁴ Chung, T.⁵ Rinker-Schaefer, C.W.⁶ Stadler, W.M.⁷

22
- 0031040640
- (1997) J. Neuro-Oncol. , vol.31 , pp. 255-266
- Pollack, I.F.¹ Kawecki, S.²

23
- 0031754283
- (1998) Clin. Can. Res. , vol.4 , pp. 2391-2398
- Dubauskas, Z.¹ Beck, T.P.² Chmura, S.J.³ Kovar, D.A.⁴ Kadkhodaian, M.M.⁵ Shrivastav, M.⁶ Chung, T.⁷ Stadler, W.M.⁸ Rinker-Schaefer, C.W.⁹

24
- 0032435749
- (1998) Clin. Can. Res. , vol.4 , pp. 2967-2976
- Zhu, D.-M.¹ Narla, R.-K.² Fang, W.-H.³ Chia, N.-C.⁴ Uckun, F.M.⁵

25
- 0032705725
- (1999) Int. J. Cancer , vol.83 , pp. 650-656
- Hochegger, K.¹ Partik, G.² Schörkhuber, M.³ Marian, B.⁴

26
- 0028218804
- (1994) Carcinogenesis , vol.15 , pp. 779-782
- Kahl, R.P.¹ Karner, H.J.² Weiss, W.³ Marian, B.⁴

27
- 0028893842
- (1995) Inflammation , vol.19 , pp. 39-54
- Hu, D.E.¹ Fan, T.-P.D.²

28
- 0032750335
- (1999) Biochem. Pharm. , vol.58 , pp. 1723-1733
- Castro, A.F.¹ Horton, J.K.² Vanoye, C.G.³ Altenberg, G.A.⁴

29
- 0027957568
- (1994) Cancer Lett. , vol.76 , pp. 139-145
- Gupta, S.¹ Patel, K.² Singh, H.³ Gollapudi, S.⁴

30
- 0030714175
- (1997) Cell. Mol. Life Sci. , vol.53 , pp. 737-743
- Murata, M.¹ Nagai, M.² Fujita, M.³ Ohmori, M.⁴ Takahara, J.⁵

31
- 0029565732
- (1995) J. Neurosurg. , vol.83 , pp. 1008-1016
- Ikemoto, H.¹ Tani, E.² Matsumoto, T.³ Nakano, A.⁴ Furuyama, J.-I.⁵

32
- 0030615399
- (1997) Can. J. Chem. , vol.75 , pp. 99-119
- Lown, J.¹

33
- 0025784927
- (1991) Biochem. Biophys. Res. Commun. , vol.176 , pp. 288-293
- Bruns, R.F.¹ Miller, F.D.² Merriman, R.L.³ Howbert, J.J.⁴ Heath, W.F.⁵ Kobayashi, E.⁶ Takahashi, I.⁷ Tamaoki, T.⁸ Nakano, H.⁹

34
- 0020419783
- (1982) Tetrahedron , vol.38 , pp. 2787-2796
- Nasini, G.¹ Merlini, L.² Andreetti, G.D.³ Bocelli, G.⁴ Sgarabotto, P.⁵

35
- 0003971643
- Wiley: New York; Chapter 14
- (1994) Stereochemistry of Carbon Compounds , pp. 1193
- Eliel, E.L.¹ Wilen, S.H.²

36
- 0033828991
- (2000) J. Org. Chem. , vol.65 , pp. 5451-5459
- Morgan, B.¹ Zaks, A.² Dodds, D.R.³ Liu, J.⁴ Jain, R.⁵ Megati, S.⁶ Njoroge, F.G.⁷ Girijavallabhan, V.M.⁸

37
- 0025325572
- (1990) J. Org. Chem. , vol.55 , pp. 3341-3350
- Piwinski, J.J.¹ Wong, J.K.² Chan, T.-M.³ Green, M.J.⁴ Ganguly, A.K.⁵

38
- 0002999412
- (1983) Top. Stereochem. , vol.13 , pp. 1-81
- Oki, M.¹

39
- 0003180127
- (1985) Top. Curr. Chem. , vol.127 , pp. 1-76
- Meurer, K.P.¹ Vögtle, F.²

40
- 0025164652
- (1990) Angew. Chem., Int. Ed. Engl. , vol.29 , pp. 977-991
- Bringmann, G.¹ Walter, R.² Weirich, R.³

41
- 0000332467
- Helmchen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: 4. Auflage, Stuttgart
- (1995) Houben-Weyl Methoden der Organischen Chemie , vol.21 Bd E , pp. 567-587
- Bringmann, G.¹ Walter, R.² Weirich, R.³

42
- 0032917881
- (1999) Synthesis , vol.4 , pp. 525-558
- Bringmann, G.¹ Breuning, M.² Tasler, S.³

43
- 0028882697
- (1995) J. Chem. Soc., Chem. Commun. , pp. 1943-1944
- Uemura, M.¹ Daimon, A.² Hayashi, Y.³

44
- 33748222146
- (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1842-1844
- Lipshutz, B.H.¹ Kayser, F.² Liu, Z.-P.³

45
- 0033532095
- (1999) Tetrahedron Lett. , vol.40 , pp. 3677-3680
- Lipshutz, B.H.¹ Müller, P.² Leinweber, D.³

46
- 0034647234
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 5656-5657
- Spring, D.R.¹ Krishnan, S.² Schreiber, S.L.³

47
- 0001428655
- (1998) J. Heterocycl. Chem. , vol.35 , pp. 991-1002
- Meyers, A.I.¹

48
- 0033620428
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 2762-2769
- Degnan, A.P.¹ Meyers, A.I.²

49
- 0025968819
- (1991) Tetrahedron Lett. , vol.32 , pp. 859-862
- Broka, C.A.¹

50
- 0029585410
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 10889-10904
- Coleman, R.S.¹ Grant, E.B.²

51
- 0027943478
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 8795-8796
- Coleman, R.S.¹ Grant, E.B.²

52
- 0027450632
- (1993) Tetrahedron Lett. , vol.34 , pp. 2225
- Coleman, R.S.¹ Grant, E.B.²

53
- 0026032673
- (1991) J. Org. Chem. , vol.56 , pp. 1357-1359
- Coleman, R.S.¹ Grant, E.B.²

54
- 0026542757
- (1992) Tetrahedron , vol.48 , pp. 45-54
- Diwu, Z.¹ Lown, J.W.²

55
- 0029127396
- (1995) Synthesis , pp. 914-916
- Liu, J.¹ Diwu, Z.² Lown, J.W.³

56
- 84986656838
- (1993) Liebigs Ann. Chem. , pp. 35-41
- Zhao, C.¹ Zhang, X.-S.² Zhang, P.³

57
- 0001399856
- (1988) Tetrahedron Lett. , vol.29 , pp. 225-226
- Chao, C.¹ Zhang, P.²

58
- 0028237470
- (1994) J. Org. Chem. , vol.59 , pp. 1967-1969
- Hauser, F.M.¹ Sengupta, D.² Corlett, S.A.³

59
- 0034607461
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 3224-3225
- Merlic, C.A.¹ Aldrich, C.C.² Albaneze-Walker, J.³ Saghatelian, A.⁴

60
- 0000489364
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 7418-7420
- Merlic, C.A.¹ Xu, D.Q.²

61
- 0027520117
- (1993) Tetrahedron Lett. , vol.34 , pp. 7379-7382
- Merlic, C.A.¹ Roberts, W.M.²

62
- 0001080334
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 8722-8724
- Merlic, C.A.¹ Burns, E.E.² Xu, D.Q.³ Chen, S.Y.⁴

63
- 0027254517
- (1993) Tetrahedron Lett. , vol.34 , pp. 5401-5404
- Merlic, C.A.¹ Burns, E.E.²

64
- 34250548658
- (1936) Monatsh. Chem. , vol.68 , pp. 51-67
- Lock, G.¹ Nottes, G.²

65
- 0039302669
- (1996) Chem. Rev. , vol.96 , pp. 2607-2624
- Que L., Jr.¹ Ho, R.Y.N.²

66
- 37049068283
- (1994) J. Chem. Soc., Chem. Commun. , pp. 1453-1454
- Funabiki, T.¹ Yoneda, I.² Ishikawa, M.³ Ujiie, M.⁴ Nagai, Y.⁵ Yoshida, S.⁶

67
- 0000380311
- (1979) Can. J. Chem. , vol.57 , pp. 1887-1889
- Miller, J.M.¹ So, K.H.² Clark, J.H.³

68
- 0006967127
- (1978) J. Organomet. Chem. , vol.156 , pp. 221-226
- Bhatt, M.V.¹

69
- 0005867543
- note

70
- 0042869554
- (1995) Chem. Rev. , vol.95 , pp. 1009-1064
- Rücker, C.¹

71
- 18844474204
- (2000) Tetrahedron , vol.56 , pp. 4967-4975
- Barluenga, J.¹ Lopez, L.A.² Martinez, S.³ Tomas, M.⁴

72
- 0005782165
- note

73
- 0005873585
- (1981) J. Org. Chem. , vol.46 , pp. 3474-3478
- Adams, S.P.¹ Whitlock H.W., Jr.²

74
- 37049097585
- (1985) J. Chem. Soc., Perkin Trans. 1 , pp. 1387
- Arnone, A.¹ Camarda, L.² Nasini, G.³

75
- 0028104478
- (1994) Tetrahedron Lett. , pp. 8111-8112
- Burk, R.M.¹ Gac, T.S.² Roof, M.B.³

76
- 33845282801
- (1987) J. Org. Chem. , vol.52 , pp. 4230-4234
- Dijkstra, G.¹ Kruizinga, W.H.² Kellogg, R.M.³

77
- 0002776196
- (1993) Synlett , pp. 913-914
- Boons, G.-J.¹ Castle, G.H.² Clase, J.A.³ Grice, P.⁴ Ley, S.V.⁵ Pinel, C.⁶

78
- 0005873588
- Wiley: New York; Collect
- (1973) Organic Syntheses , vol.6 , pp. 800-803

79
- 0005868129
- note

80
- 0032474799
- (1998) Tetrahedron Lett. , vol.39 , pp. 4883-4886
- Basak, A.¹ Nayak, M.K.² Chakraborti, A.K.³

81
- 0001333615
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 3357-3366
- Feldman, K.S.¹ Ensel, S.M.²

82
- 0030013644
- (1996) J. Org. Chem. , vol.61 , pp. 2606-2612
- Feldman, K.S.¹ Smith, R.S.²

83
- 0000547277
- (1988) Bull. Chem. Soc. Jpn. , vol.61 , pp. 3249-3254
- Miyano, S.¹ Fukushima, H.² Handa, S.³ Ito, H.⁴ Hashimoto, H.⁵

84
- 0005833656
- See ref 28

85
- 0005833657
- Wavefunction Inc., 18401 Von Karman Ave., Suite 370, Irvine, CA 92612
- (1840) Spartan, SGI Version 5.0

86
- 0029799743
- (1996) Angew. Chem., Int. Ed. , vol.35 , pp. 2056-2083
- Schelhaas, M.¹ Waldmann, H.²

87
- 0005874115
- note

88
- 0005821997
- note

89
- 0005861620
- note

90
- 0011475687
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 5330-5331
- Cozzi, F.¹ Cinquini, M.² Annuziata, R.³ Siegel, J.S.⁴

91
- 0005783560
- note

92
- 0005861622
- note

93
- 0005859123
- Hagemann, H., Ed.; Georg Thieme Verlag: 4. Auflage, Stuttgart
- (1983) Houben-Weyl Methoden der Organischen Chemie , vol.4 Bd E , pp. 66-77
- Petersen, U.¹

94
- 0033536670
- (1999) Tetrahedron Lett. , vol.40 , pp. 7363-7365
- Yamaguchi, S.¹ Nedachi, M.² Yokoyama, H.³ Hirai, Y.⁴

95
- 0026494593
- (1992) Photochem. Photobiol. , vol.55 , pp. 145-157
- Henderson, B.W.¹ Dougherty, T.J.²

96
- 0032802212
- (1999) Pharm. Res. , vol.16 , pp. 1003-1009
- Chen, C.-L.¹ Tai, H.-L.² Zhu, D.-M.³ Uckun, F.M.⁴

97
- 0032538575
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2700-2704
- Evans, D.A.¹ Wood, M.R.² Trotter, B.W.³ Richardson, T.I.⁴ Barrow, J.C.⁵ Katz, J.L.⁶

98
- 0032538360
- (1998) Angew. Chem., Int. Ed. , vol.37 , pp. 2704-2708
- Evans, D.A.¹ Dinsmore, C.J.² Watson, P.S.³ Wood, M.R.⁴ Richardson, T.I.⁵ Trotter, B.W.⁶ Katz, J.L.⁷

99
- 0033531677
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 3226-3227
- Boger, D.L.¹ Miyazaki, S.² Kim, S.H.³ Wu, J.H.⁴ Loiseleur, O.⁵ Castle, S.L.⁶

100
- 0033534565
- (1999) J. Org. Chem. , vol.64 , pp. 70-80
- Boger, D.L.¹ Castle, S.L.² Miyazaki, S.³ Wu, J.H.⁴ Beresis, R.T.⁵ Loiseleur, O.⁶

101
- 0033584943
- (1999) Tetrahedron Lett. , vol.40 , pp. 8281-8285
- Yoshimura, F.¹ Kawata, S.² Hirama, M.³

102
- 0033521225
- (1999) Angew. Chem., Int. Ed. Engl. , vol.38 , pp. 3530-3533
- Lipshutz, B.H.¹ Keith, J.M.²

103
- 0001498370
- (1986) Tetrahedron Lett. , vol.27 , pp. 1785-1788
- Landais, Y.¹ Robin, J.-P.²

104
- 0012709868
- Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon Press
- (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 491-497
- Wulff, W.D.¹

105
- 0031585112
- (1997) Tetrahedron , vol.53 , pp. 4105-4128
- Hegedus, L.S.¹

106
- 0005781515
- See the Supporting Information

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