SCOPUS 정보 검색 플랫폼

Helvetica Chimica Acta

Volumn 86, Issue 6, 2003, Pages 1871-1893

Synthesis and conformational analysis of macrocyclic dilactones mimicking the pharmacophore of aplysiatoxin

(2) Knust, Henner a Hoffmann, Reinhard W a

a PHILIPPS UNIVERSITY MARBURG (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

CONFORMATIONS; ORGANIC ACIDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

CONFORMATIONAL ANALYSIS;

KETONES;

APLYSIATOXIN; LACTONE; MACROCYCLIC COMPOUND;

ANALYTIC METHOD; ARTICLE; CONFORMATIONAL TRANSITION; CRYSTAL STRUCTURE; MOLECULAR INTERACTION; MOLECULAR RECOGNITION; NUCLEAR MAGNETIC RESONANCE; PHARMACOPHORE; PRIORITY JOURNAL; PROTEIN DOMAIN; SOLID STATE; STEREOCHEMISTRY; SYNTHESIS;

EID: 0042806062 PISSN: 0018019X EISSN: None Source Type: Journal
DOI: 10.1002/hlca.200390151 Document Type: Article

Times cited : (16)

References (51)

1
- 0016383533
- Y. Kato, P. J. Scheuer, J. Am. Chem. Soc. 1974, 96, 2245.
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 2245
- Kato, Y.¹ Scheuer, P.J.²

2
- 0024819506
- H. Nakamura, Y. Kishi, M. A. Pajares, R. R. Rando, Proc. Natl. Acad. Sci. U.S.A. 1989, 86, 9672.
- (1989) Proc. Natl. Acad. Sci. U.S.A. , vol.86 , pp. 9672
- Nakamura, H.¹ Kishi, Y.² Pajares, M.A.³ Rando, R.R.⁴

3
- 0000306618
- Y. Kishi, R. R. Rando, Acc. Chem. Res. 1998, 31, 163.
- (1998) Acc. Chem. Res. , vol.31 , pp. 163
- Kishi, Y.¹ Rando, R.R.²

4
- 0026022619
- F. Kong, Y. Kishi, D. Perez-Sala, R. R. Rando, Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 1973.
- (1991) Proc. Natl. Acad. Sci. U.S.A. , vol.88 , pp. 1973
- Kong, F.¹ Kishi, Y.² Perez-Sala, D.³ Rando, R.R.⁴

5
- 33845471434
- R. E. Moore, A. J. Blackman, C. E. Cheuk, J. S. Mynderse, G. K. Matsumoto, J. S. Clardy, R. W. Woodard, J. C. Craig, J. Org. Chem. 1984, 49, 2484.
- (1984) J. Org. Chem. , vol.49 , pp. 2484
- Moore, R.E.¹ Blackman, A.J.² Cheuk, C.E.³ Mynderse, J.S.⁴ Matsumoto, G.K.⁵ Clardy, J.S.⁶ Woodard, R.W.⁷ Craig, J.C.⁸

6
- 0000172608
- W. C. Still, L. J. MacPherson, T. Harada, J. F. Callahan, A. L. Rheingold, Tetrahedron 1984, 40, 2275;
- (1984) Tetrahedron , vol.40 , pp. 2275
- Still, W.C.¹ MacPherson, L.J.² Harada, T.³ Callahan, J.F.⁴ Rheingold, A.L.⁵

7
- 1542532787
- W. C. Still, I. Galynker, Tetrahedron 1981, 37, 3981.
- (1981) Tetrahedron , vol.37 , pp. 3981
- Still, W.C.¹ Galynker, I.²

8
- 0010783788
- J. T. B. Ferreira, E. G. Neeland, J. P. Ounsworth, L. Weiler, Can. J. Chem. 1987, 65, 2314;
- (1987) Can. J. Chem. , vol.65 , pp. 2314
- Ferreira, J.T.B.¹ Neeland, E.G.² Ounsworth, J.P.³ Weiler, L.⁴

9
- 0000968871
- T. H. Keller, E. G. Neeland, S. Rettig, J. Trotter, L. Weiler, J. Am. Chem. Soc. 1988, 110, 7858;
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 7858
- Keller, T.H.¹ Neeland, E.G.² Rettig, S.³ Trotter, J.⁴ Weiler, L.⁵

10
- 0025278271
- T. H. Keller, L. Weiler, J. Am. Chem. Soc. 1990, 112, 450.
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 450
- Keller, T.H.¹ Weiler, L.²

11
- 0042540237
- J. Dale, J. Chem. Soc. 1963, 93; J. Dale, Angew. Chem. 1966, 78, 1070; Angew. Chem., Int. Ed. 1966, 5, 1000; J. Dale. Acta. Chem. Scand. 1973, 27, 1115; F. A. L. Anet, A. K. Cheng, J. Am. Chem. Soc. 1975, 97, 2420; F. A. L. Anet, T. N. Rawdah, J. Am. Chem. Soc. 1978, 100, 7810.
- (1963) J. Chem. Soc. , vol.93
- Dale, J.¹

12
- 0001704530
- J. Dale, J. Chem. Soc. 1963, 93; J. Dale, Angew. Chem. 1966, 78, 1070; Angew. Chem., Int. Ed. 1966, 5, 1000; J. Dale. Acta. Chem. Scand. 1973, 27, 1115; F. A. L. Anet, A. K. Cheng, J. Am. Chem. Soc. 1975, 97, 2420; F. A. L. Anet, T. N. Rawdah, J. Am. Chem. Soc. 1978, 100, 7810.
- (1966) Angew. Chem. , vol.78 , pp. 1070
- Dale, J.¹

13
- 84980966357
- J. Dale, J. Chem. Soc. 1963, 93; J. Dale, Angew. Chem. 1966, 78, 1070; Angew. Chem., Int. Ed. 1966, 5, 1000; J. Dale. Acta. Chem. Scand. 1973, 27, 1115; F. A. L. Anet, A. K. Cheng, J. Am. Chem. Soc. 1975, 97, 2420; F. A. L. Anet, T. N. Rawdah, J. Am. Chem. Soc. 1978, 100, 7810.
- (1966) Angew. Chem., Int. Ed. , vol.5 , pp. 1000

14
- 0042540236
- J. Dale, J. Chem. Soc. 1963, 93; J. Dale, Angew. Chem. 1966, 78, 1070; Angew. Chem., Int. Ed. 1966, 5, 1000; J. Dale. Acta. Chem. Scand. 1973, 27, 1115; F. A. L. Anet, A. K. Cheng, J. Am. Chem. Soc. 1975, 97, 2420; F. A. L. Anet, T. N. Rawdah, J. Am. Chem. Soc. 1978, 100, 7810.
- (1973) J. Dale. Acta. Chem. Scand. , vol.27 , pp. 1115

15
- 0000772387
- J. Dale, J. Chem. Soc. 1963, 93; J. Dale, Angew. Chem. 1966, 78, 1070; Angew. Chem., Int. Ed. 1966, 5, 1000; J. Dale. Acta. Chem. Scand. 1973, 27, 1115; F. A. L. Anet, A. K. Cheng, J. Am. Chem. Soc. 1975, 97, 2420; F. A. L. Anet, T. N. Rawdah, J. Am. Chem. Soc. 1978, 100, 7810.
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 2420
- Anet, F.A.L.¹ Cheng, A.K.²

16
- 0000448880
- J. Dale, J. Chem. Soc. 1963, 93; J. Dale, Angew. Chem. 1966, 78, 1070; Angew. Chem., Int. Ed. 1966, 5, 1000; J. Dale. Acta. Chem. Scand. 1973, 27, 1115; F. A. L. Anet, A. K. Cheng, J. Am. Chem. Soc. 1975, 97, 2420; F. A. L. Anet, T. N. Rawdah, J. Am. Chem. Soc. 1978, 100, 7810.
- (1978) J. Am. Chem. Soc. , vol.100 , pp. 7810
- Anet, F.A.L.¹ Rawdah, T.N.²

17
- 0000314027
- R. W. Hoffmann, Angew. Chem. 1992, 104, 1147; Angew. Chem., Int. Ed. 1992, 31, 1124; R. W. Hoffmann, M. Stahl, U. Schopfer, G. Frenking, Chem.-Eur. J. 1998, 4, 559; R. W. Hoffmann, Angew. Chem. 2000, 112, 2134; Angew. Chem., Int. Ed. 2000, 39, 2054.
- (1992) Angew. Chem. , vol.104 , pp. 1147
- Hoffmann, R.W.¹

18
- 0026640040
- R. W. Hoffmann, Angew. Chem. 1992, 104, 1147; Angew. Chem., Int. Ed. 1992, 31, 1124; R. W. Hoffmann, M. Stahl, U. Schopfer, G. Frenking, Chem.-Eur. J. 1998, 4, 559; R. W. Hoffmann, Angew. Chem. 2000, 112, 2134; Angew. Chem., Int. Ed. 2000, 39, 2054.
- (1992) Angew. Chem., Int. Ed. , vol.31 , pp. 1124

19
- 0031833483
- R. W. Hoffmann, Angew. Chem. 1992, 104, 1147; Angew. Chem., Int. Ed. 1992, 31, 1124; R. W. Hoffmann, M. Stahl, U. Schopfer, G. Frenking, Chem.-Eur. J. 1998, 4, 559; R. W. Hoffmann, Angew. Chem. 2000, 112, 2134; Angew. Chem., Int. Ed. 2000, 39, 2054.
- (1998) Chem.-Eur. J. , vol.4 , pp. 559
- Hoffmann, R.W.¹ Stahl, M.² Schopfer, U.³ Frenking, G.⁴

20
- 0000223068
- R. W. Hoffmann, Angew. Chem. 1992, 104, 1147; Angew. Chem., Int. Ed. 1992, 31, 1124; R. W. Hoffmann, M. Stahl, U. Schopfer, G. Frenking, Chem.-Eur. J. 1998, 4, 559; R. W. Hoffmann, Angew. Chem. 2000, 112, 2134; Angew. Chem., Int. Ed. 2000, 39, 2054.
- (2000) Angew. Chem. , vol.112 , pp. 2134
- Hoffmann, R.W.¹

21
- 0034674252
- R. W. Hoffmann, Angew. Chem. 1992, 104, 1147; Angew. Chem., Int. Ed. 1992, 31, 1124; R. W. Hoffmann, M. Stahl, U. Schopfer, G. Frenking, Chem.-Eur. J. 1998, 4, 559; R. W. Hoffmann, Angew. Chem. 2000, 112, 2134; Angew. Chem., Int. Ed. 2000, 39, 2054.
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2054

22
- 0343550407
- D. S. Clyne, L. Weiler, Tetrahedron 2000, 56, 1281.
- (2000) Tetrahedron , vol.56 , pp. 1281
- Clyne, D.S.¹ Weiler, L.²

23
- 0042039367
- Dissertation, Universität Marburg
- H. Knust, Dissertation, Universität Marburg, 2001.
- (2001)
- Knust, H.¹

24
- 0001006163
- T. R. Kelly, P. N. Kaul, J. Org. Chem. 1983, 48, 2775; D. C. Baker, L. D. Hawkins, J. Org. Chem. 1982, 47, 2179.
- (1983) J. Org. Chem. , vol.48 , pp. 2775
- Kelly, T.R.¹ Kaul, P.N.²

25
- 0001556230
- T. R. Kelly, P. N. Kaul, J. Org. Chem. 1983, 48, 2775; D. C. Baker, L. D. Hawkins, J. Org. Chem. 1982, 47, 2179.
- (1982) J. Org. Chem. , vol.47 , pp. 2179
- Baker, D.C.¹ Hawkins, L.D.²

26
- 33845470995
- C. H. Heathcock, S.-I. Kiyooka, T. A. Blumenkopf, J. Org. Chem. 1984, 49, 4214.
- (1984) J. Org. Chem. , vol.49 , pp. 4214
- Heathcock, C.H.¹ Kiyooka, S.-I.² Blumenkopf, T.A.³

27
- 37049110000
- C. A. Cornish, S. Warren, J. Chem. Soc., Perkin Trans. 1 1985, 2585.
- (1985) J. Chem. Soc., Perkin Trans. 1 , pp. 2585
- Cornish, C.A.¹ Warren, S.²

28
- 0026774450
- D. H. R. Barton, J. Zhu, Tetrahedron 1992, 48, 8337.
- (1992) Tetrahedron , vol.48 , pp. 8337
- Barton, D.H.R.¹ Zhu, J.²

29
- 0001616071
- J. Inanaga, K. Hirata, H. Saeki, T. Katsuki, M. Yamaguchi, Bull. Chem. Soc. Jpn. 1979, 52, 1989.
- (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 1989
- Inanaga, J.¹ Hirata, K.² Saeki, H.³ Katsuki, T.⁴ Yamaguchi, M.⁵

30
- 0034685462
- A. K. Chatterjee, J. P. Morgan, M. Scholl, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 3783; C. W. Lee, R. H. Grubbs, J. Org. Chem. 2001, 66, 7155.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 3783
- Chatterjee, A.K.¹ Morgan, J.P.² Scholl, M.³ Grubbs, R.H.⁴

31
- 0035914011
- A. K. Chatterjee, J. P. Morgan, M. Scholl, R. H. Grubbs, J. Am. Chem. Soc. 2000, 122, 3783; C. W. Lee, R. H. Grubbs, J. Org. Chem. 2001, 66, 7155.
- (2001) J. Org. Chem. , vol.66 , pp. 7155
- Lee, C.W.¹ Grubbs, R.H.²

32
- 0037620216
- A. Fürstner, O. R. Thiel, L. Ackermann, H.-J. Schanz, S. P. Nolan, J. Org. Chem. 2000, 65, 2204.
- (2000) J. Org. Chem. , vol.65 , pp. 2204
- Fürstner, A.¹ Thiel, O.R.² Ackermann, L.³ Schanz, H.-J.⁴ Nolan, S.P.⁵

33
- 33751385839
- G. A. Molander, K. O. Cameron, J. Org. Chem. 1993, 58, 5931.
- (1993) J. Org. Chem. , vol.58 , pp. 5931
- Molander, G.A.¹ Cameron, K.O.²

34
- 33847797434
- D. F. Taber, J. Org. Chem. 1976, 41, 2649.
- (1976) J. Org. Chem. , vol.41 , pp. 2649
- Taber, D.F.¹

35
- 0001484430
- N. Krause, Angew. Chem. 1994, 106, 1845;
- (1994) Angew. Chem. , vol.106 , pp. 1845
- Krause, N.¹

36
- 33749027108
- Angew. Chem., Int. Ed. 1994, 33, 1764.
- (1994) Angew. Chem., Int. Ed. , vol.33 , pp. 1764

37
- 0000169587
- T. Tsunoda, M. Suzuki, R. Noyori, Tetrahedron Lett. 1980, 21, 1357.
- (1980) Tetrahedron Lett. , vol.21 , pp. 1357
- Tsunoda, T.¹ Suzuki, M.² Noyori, R.³

38
- 0000491860
- M. T. Reetz, B. Raguse, C. F. Marth, H. M. Hügel, T. Bach, D. N. A. Fox, Tetrahedron 1992, 48, 5731.
- (1992) Tetrahedron , vol.48 , pp. 5731
- Reetz, M.T.¹ Raguse, B.² Marth, C.F.³ Hügel, H.M.⁴ Bach, T.⁵ Fox, D.N.A.⁶

39
- 0033525048
- N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, K. Tachibana, J. Org. Chem. 1999, 64, 866.
- (1999) J. Org. Chem. , vol.64 , pp. 866
- Matsumori, N.¹ Kaneno, D.² Murata, M.³ Nakamura, H.⁴ Tachibana, K.⁵

40
- 0037043503
- P. Cimino, G. Bifulco, A. Evidente, A. Abouzeid, R. Riccio, L. Gomez-Paloma, Org. Lett. 2002, 4, 2779.
- (2002) Org. Lett. , vol.4 , pp. 2779
- Cimino, P.¹ Bifulco, G.² Evidente, A.³ Abouzeid, A.⁴ Riccio, R.⁵ Gomez-Paloma, L.⁶

41
- 0000516598
- C. A. Podlasek, J. Wu, W. A. Stripe, P. B. Bondo, A. S. Serianni, J. Am. Chem. Soc. 1995, 117, 8635; H. Ikeda, N. Matsumori, M. Ono, A. Suzuki, A. Isogai, H. Nagasawa, S. Sakuda, J. Org. Chem. 2000, 65, 438.
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 8635
- Podlasek, C.A.¹ Wu, J.² Stripe, W.A.³ Bondo, P.B.⁴ Serianni, A.S.⁵

42
- 0034723341
- C. A. Podlasek, J. Wu, W. A. Stripe, P. B. Bondo, A. S. Serianni, J. Am. Chem. Soc. 1995, 117, 8635; H. Ikeda, N. Matsumori, M. Ono, A. Suzuki, A. Isogai, H. Nagasawa, S. Sakuda, J. Org. Chem. 2000, 65, 438.
- (2000) J. Org. Chem. , vol.65 , pp. 438
- Ikeda, H.¹ Matsumori, N.² Ono, M.³ Suzuki, A.⁴ Isogai, A.⁵ Nagasawa, H.⁶ Sakuda, S.⁷

43
- 20444483055
- C. A. G. M. Haasnoot, F. A. A. de Leeuw, C. Altona, Tetrahedron 1980, 36, 2783; P. E. Hansen, Prog. NMR Spectrosc. 1981, 14, 175.
- (1980) Tetrahedron , vol.36 , pp. 2783
- Haasnoot, C.A.G.M.¹ De Leeuw, F.A.A.² Altona, C.³

44
- 49149139337
- C. A. G. M. Haasnoot, F. A. A. de Leeuw, C. Altona, Tetrahedron 1980, 36, 2783; P. E. Hansen, Prog. NMR Spectrosc. 1981, 14, 175.
- (1981) Prog. NMR Spectrosc. , vol.14 , pp. 175
- Hansen, P.E.¹

45
- 0025252231
- G. Otting, K. Wüthrich, Quart. Rev. Biophys. 1990, 23, 39; M. Kurz, P. Schmieder, H. Kessler, Angew. Chem. 1991, 103, 1341; Angew. Chem., Int. Ed. 1991, 30, 1329; U. Wollborn, D. J. Leibfritz, J. Magn. Reson. 1992, 98, 142.
- (1990) Quart. Rev. Biophys. , vol.23 , pp. 39
- Otting, G.¹ Wüthrich, K.²

46
- 0025252231
- G. Otting, K. Wüthrich, Quart. Rev. Biophys. 1990, 23, 39; M. Kurz, P. Schmieder, H. Kessler, Angew. Chem. 1991, 103, 1341; Angew. Chem., Int. Ed. 1991, 30, 1329; U. Wollborn, D. J. Leibfritz, J. Magn. Reson. 1992, 98, 142.
- (1991) Angew. Chem. , vol.103 , pp. 1341
- Kurz, M.¹ Schmieder, P.² Kessler, H.³

47
- 33748245805
- G. Otting, K. Wüthrich, Quart. Rev. Biophys. 1990, 23, 39; M. Kurz, P. Schmieder, H. Kessler, Angew. Chem. 1991, 103, 1341; Angew. Chem., Int. Ed. 1991, 30, 1329; U. Wollborn, D. J. Leibfritz, J. Magn. Reson. 1992, 98, 142.
- (1991) Angew. Chem., Int. Ed. , vol.30 , pp. 1329

48
- 0001596822
- G. Otting, K. Wüthrich, Quart. Rev. Biophys. 1990, 23, 39; M. Kurz, P. Schmieder, H. Kessler, Angew. Chem. 1991, 103, 1341; Angew. Chem., Int. Ed. 1991, 30, 1329; U. Wollborn, D. J. Leibfritz, J. Magn. Reson. 1992, 98, 142.
- (1992) J. Magn. Reson. , vol.98 , pp. 142
- Wollborn, U.¹ Leibfritz, D.J.²

49
- 1542784335
- R. Göttlich, B. C. Kahrs, J. Krüger, R. W. Hoffmann, Chem. Commun. 11997, 247.
- (1997) Chem. Commun. 1 , pp. 247
- Göttlich, R.¹ Kahrs, B.C.² Krüger, J.³ Hoffmann, R.W.⁴

50
- 0042039364
- H. Knust, R. W. Hoffmann, Chem. Rec. 2002, 2, 405.
- (2002) Chem. Rec. , vol.2 , pp. 405
- Knust, H.¹ Hoffmann, R.W.²

51
- 0041538144
- D. P. Brust, D. S. Tarbell, J. Org. Chem. 1966, 31, 1251.
- (1966) J. Org. Chem. , vol.31 , pp. 1251
- Brust, D.P.¹ Tarbell, D.S.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.