SCOPUS 정보 검색 플랫폼

Journal of Organic Chemistry

Volumn 66, Issue 4, 2001, Pages 1082-1096

Synthesis and ring contraction reactions of polyazamacrolides

(2) Garcia Rubio S a Meinwald, J a

a Department of Obstetrics Gynecology (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROXYACID; MACROCYCLIC COMPOUND; MACROLIDE; NITROGEN; OXYGEN; POLYAZAMACROLIDE; SULFUR DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BEETLE; CHEMICAL STRUCTURE; NONHUMAN; OLIGOMERIZATION; REACTION ANALYSIS; REACTION TIME; SECRETION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS;

ANIMALS; BEETLES; CHROMATOGRAPHY, HIGH PRESSURE LIQUID; MACROLIDES; MASS SPECTROMETRY; MOLECULAR STRUCTURE;

EID: 0035936806 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo001247h Document Type: Article

Times cited : (9)

References (103)

1
- 0005820410
- (1995) Proc. Natl. Acad. Sci. U.S.A. , vol.92 , pp. 12
- Meinwald, J.¹ Eisner, T.²

2
- 0001408338
- (1996) Chem. Rev. , vol.96 , pp. 1105
- King, A.G.¹ Meinwald, J.²

3
- 0027279051
- (1993) Proc. Natl. Acad. Sci. U.S.A. , vol.90 , pp. 5204
- Attygalle, A.B.¹ McCormick, K.D.² Blankespoor, C.L.³ Eisner, T.⁴ Meinwald, J.⁵

4
- 0029957812
- (1996) Experientia , vol.52 , pp. 616
- Attygalle, A.B.¹ Smedley, S.² Eisner, T.³ Meinwald, J.⁴

5
- 0032506026
- (1998) Proc. Natl. Acad. Sci. U.S.A. , vol.95 , pp. 13387
- Schröder, F.¹ Smedley, S.² Gibbons, L.K.³ Farmer, J.⁴ Attygalle, A.⁵ Eisner, T.⁶ Meinwald, J.⁷

6
- 0005873180
- (2000) J. Org. Chem. , vol.2 , pp. 1075
- Gronquist, M.R.¹ Meinwald, J.²

7
- 0040364379
- (1998) Science , vol.281 , pp. 428
- Schröder, F.¹ Farmer, J.² Attygalle, A.³ Smedley, S.⁴ Eisner, T.⁵ Meinwald, J.⁶

8
- 0034685465
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 3628
- Schröder, F.¹ Farmer, J.² Smedley, S.³ Attygalle, A.⁴ Eisner, T.⁵ Meinwald, J.⁶

9
- 0343196694
- (1997) Tetrahedron Lett. , vol.38 , pp. 2787
- Farmer, J.¹ Attygalle, A.² Smedley, S.³ Eisner, T.⁴ Meinwald, J.⁵

10
- 0033791086
- (2000) Helv. Chim. Acta , vol.83 , pp. 2594
- Farmer, J.¹ Schröder, F.² Meinwald, J.³

11
- 0005855781
- (1966) Chem. Ber. , vol.99 , pp. 3173
- Adam, G.¹ Schreiber, K.²

12
- 0014369367
- (1968) Proc. Natl. Acad. Sci. U.S.A. , vol.61 , pp. 1207
- Neumann, H.¹ Shashoua, V.E.² Sheehan, J.C.³ Rich, A.⁴

13
- 0029810364
- (1996) Helv. Chim. Acta , vol.79 , pp. 1635
- Pohl, E.¹ Sheldrick, G.M.² Bölsterli, J.J.³ Kallen, J.⁴ Traber, R.⁵ Walkinshaw, M.D.⁶

14
- 0028299778
- (1994) Int. J. Peptide Protein Res. , vol.43 , pp. 239
- Oliyai, R.¹ Safadi, M.² Meier, P.G.³ Hu, M.K.⁴ Rich, D.H.⁵ Stella, V.J.⁶

15
- 0017072249
- (1976) Helv. Chim. Acta , vol.59 , pp. 1075
- Rüegger, A.¹ Kuhn, M.² Lichti, H.³ Loosli, H.R.⁴ Hugenin, R.⁵ Quiquerez, C.⁶ Von Wartburg, A.⁷

16
- 0028847274
- (1995) Bioorg. Med. Chem. Lett. , vol.5 , pp. 2735
- Oliyai, R.¹ Stella, V.J.²

17
- 0034717002
- (2000) Tetrahedron , vol.56 , pp. 3449
- Coltart, D.M.¹

18
- 0033657692
- (2000) Org. Lett. , vol.2 , pp. 23
- Offer, J.¹ Dawson, P.E.²

19
- 0033549108
- and references therein
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 4316
- Tam, J.P.¹ Lu, Y.-A.² Yu, Q.³

20
- 84985687610
- (1981) Biopolymers , vol.20 , pp. 1793
- Kemp, D.S.¹

21
- 0000605733
- (1981) J. Org. Chem. , vol.46 , pp. 490
- Kemp, D.S.¹ Kerkman, D.J.² Leung, S.L.³ Hanson, G.⁴

22
- 0016851756
- (1975) J. Org. Chem. , vol.40 , pp. 3464
- Kemp, D.S.¹ Vellaccio, F.²

23
- 33947476461
- (1962) J. Am. Chem. Soc. , vol.84 , pp. 4921
- Sakakibara, S.¹ Shin, K.H.² Hess, G.P.³

24
- 0032506677
- (1998) Tetrahedron Lett. , vol.39 , pp. 9309
- Derrer, S.¹ Feeder, N.² Teat, S.J.³ Davies, J.E.⁴ Holmes, A.B.⁵

25
- 0033575092
- and references therein
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 5597
- Camarero, J.A.¹ Muir, T.W.²

26
- 0029916431
- (1996) Tetrahedron Lett. , vol.37 , pp. 2145
- Gribble, G.W.¹ Silva, R.A.²

27
- 0001464540
- (1989) J. Org. Chem. , vol.54 , pp. 1430
- Flippin, L.A.¹ Gallagher, D.W.² Jalali-Araghi, K.³

28
- 0001019593
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 9925
- Holt, A.D.¹ Luengo, J.I.² Yamashita, D.S.³ Oh, H.-J.⁴ Konialian, A.L.⁵ Yen, H.-K.⁶ Rozamus, L.W.⁷ Brandt, M.⁸ Bossard, M.J.⁹ Levy, M.A.¹⁰ Eggleston, D.S.¹¹ Liang, J.¹² Schultz, L.W.¹³ Stout, T.J.¹⁴ Clardy, J.¹⁵

29
- 0027997412
- (1994) Synthesis , pp. 639
- Ley, S.V.¹ Norman, J.² Griffith, W.P.³ Mardsen, S.P.⁴

30
- 0033516518
- (1999) Tetrahedron Lett. , vol.40 , pp. 4965
- Lu, W.¹ Sih, C.J.²

31
- 0019439350
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 3213
- Woodward, R.B.¹

32
- 0001649196
- (1982) J. Org. Chem. , vol.47 , pp. 1962
- Dhaon, M.K.¹ Olsen, R.K.² Ramasamy, K.³

33
- 84944588148
- (1984) Synth. Commun. , vol.14 , pp. 515
- Balleste-Rodes, M.¹ Palomo-Coll, A.L.²

34
- 0001616071
- (1979) Bull. Chem. Soc. Jpn. , vol.52 , pp. 1989
- Inanaga, J.¹ Hirata, K.² Saeki, H.³ Katsuki, T.⁴ Yamaguchi, M.⁵

35
- 0025775820
- (1991) Tetrahedron , vol.47 , pp. 5625
- Ramage, R.¹ MacLeod, A.M.² Rose, G.W.³

36
- 33748448195
- (1978) Tetrahedron Lett. , vol.46 , pp. 4475
- Hassner, A.¹ Alexanian, V.²

37
- 0029841253
- (1996) Synthesis , pp. 1031
- Nelson, T.D.¹ Crouch, R.D.²

38
- 0005781925
- Protective Groups in Organic Synthesis, 3rd ed.; Wiley & Sons: New York, Chapter 7
- (1999) , pp. 518
- Greene, T.W.¹ Wuts, P.G.-M.²

39
- 0003105165
- (1976) Chem. Lett. , pp. 49
- Mukaiyama, T.¹ Usui, M.² Saigo, K.³

40
- 0000035304
- (1992) J. Org. Chem. , vol.57 , pp. 2771
- Askin, D.¹ Wallace, M.A.² Vacca, J.P.³ Reamer, R.A.⁴ Volante, R.P.⁵ Shinkai, I.⁶

41
- 33751392677
- (1992) Inorg. Chem. , vol.31 , pp. 3636
- Alul, R.¹ Cleaver, M.B.² Taylor, J.-S.³

42
- 0025279957
- (1990) Tetrahedron Lett. , vol.31 , pp. 3745
- Sha, C.K.¹ Tsong Shin, J.² Wang, D.C.³

43
- 0026568993
- (1992) Tetrahedron , vol.48 , pp. 2359
- Lin, P.-Y.¹ Bellos, K.² Stamm, H.³ Onistschenko, A.⁴

44
- 0000323135
- (1987) Tetrahedron , vol.43 , pp. 565
- Onistschenko, A.¹ Buchholz, B.² Stamm, H.³

45
- 0000913878
- (1982) Tetrahedron Lett. , vol.23 , pp. 5021
- Stamm, H.¹ Assithianakis, P.² Buchholz, B.³ Weib, R.⁴

46
- 33845185293
- (1989) J. Org. Chem. , vol.59 , pp. 1548
- Heathcock, C.H.¹ Blumenkopf, T.A.² Smith, K.M.³

47
- 0000558372
- (1993) J. Org. Chem. , vol.58 , pp. 1604
- Guziek, F.S.¹ Torres, F.F.²

48
- 0029132233
- (1995) Tetrahedron Lett. , vol.36 , pp. 6013
- Kim, H.-O.¹ Gardner, B.² Kahn, M.³

49
- 0005873182
- (1995) Synlett , pp. 549
- Kim, H.-O.¹ Kahn, M.²

50
- 0005823173
- Ph.D. Thesis, Cornell University
- (1999)
- Farmer, J.J.¹

51
- 0007703584
- Wiley & Sons: New York, Chapter 7
- (1999) Protective Groups in Organic Synthesis, 3rd ed , pp. 415

52
- 0000117881
- (1996) J. Org. Chem. , vol.61 , pp. 8402
- Marcovici-Mizrahi, D.¹ Gottlieb, H.E.² Marks, V.³ Nudelman, A.⁴

53
- 0000459942
- (1998) J. Org. Chem. , vol.63 , pp. 7258
- Moraczevski, A.L.¹ Banaszynski, L.A.² From, A.M.³ White, C.E.⁴ Smith, B.D.⁵

54
- 0001218176
- (1985) J. Org. Chem. , vol.50 , pp. 5032
- Sugg, E.E.¹ Griffin, J.F.² Portoghese, P.S.³

55
- 33845374692
- (1986) J. Org. Chem. , vol.51 , pp. 4000
- Soai, K.¹ Ookawa, A.²

56
- 0005782286
- note

57
- 0003440569
- and references therein
- (1980) Adv. Phys. Org. Chem. , pp. 183
- Kirby, A.J.¹

58
- 0034674693
- (2000) J. Org. Chem. , vol.65 , pp. 3579
- Fife, T.H.¹ Chauffe, L.²

59
- 0002590924
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 74
- Fife, T.H.¹ Duddy, N.W.²

60
- 33947485629
- (1963) J. Am. Chem. Soc. , vol.85 , pp. 1
- Bruice, T.C.¹ Benkovic, S.J.²

61
- 0005781610
- W. A. Benjamin: New York
- (1966) Bioorganic Mechanisms , vol.1
- Bruice, T.C.¹ Benkovic, S.J.²

62
- 33748939157
- (1915) J. Chem. Soc. , vol.107 , pp. 1080
- Beesley, R.M.¹ Ingold, C.K.² Thorpe, J.F.³

63
- 37049160989
- (1921) J. Chem. Soc. , vol.119 , pp. 305
- Ingold, C.K.¹

64
- 0004028219
- Newman, M. S., Ed.; Wiley: New York
- (1956) Steric Effects in Organic Chemistry
- Hammond, G.S.¹

65
- 0000110272
- (1960) J. Org. Chem. , vol.25 , pp. 701
- Allinger, N.L.¹ Zalkow, V.²

66
- 85023100437
- (1960) J. Am. Chem. Soc. , vol.82 , pp. 5858
- Bruice, T.C.¹ Pandit, U.K.²

67
- 15044349560
- (1961) J. Am. Chem. Soc. , vol.83 , pp. 1368
- Schleyer, P.V.R.¹

68
- 0028095190
- (1994) Tetrahedron Lett. , vol.35 , pp. 7319
- Parrill, A.L.¹ Dolata, D.P.²

69
- 0005821926
- (1996) THEOCHEM, J. Mol. Struct. , vol.370 , pp. 182
- Parrill, A.L.¹ Dolata, D.P.²

70
- 0033011059
- (1999) Synlett , pp. 843
- Jung, M.E.¹

71
- 0003971643
- McGraw-Hill: New York
- (1962) Stereochemistry of Carbon Compounds , pp. 197
- Eliel, E.¹

72
- 0003846387
- Plenum Press: New York
- (1976) Neighboring Group Participation , vol.1 , pp. 43
- Capon, B.¹ Mc-Manus, S.P.²

73
- 0001609007
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 224
- Jung, M.E.¹ Gervay, J.²

74
- 0027418814
- and references therein
- (1993) Tetrahedron , vol.49 , pp. 2055
- Keese, R.¹ Meyer, M.²

75
- 0005821928
- note

76
- 0007793280
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 1419
- Saunders, M.¹ Houk, K.N.² Wu, Y.-D.³ Still, C.⁴ Lipton, M.⁵ Chang, G.⁶ Guida, W.C.⁷

77
- 11744387198
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 3150
- Saunders, M.¹

78
- 0034647513
- (2000) Tetrahedron , vol.56 , pp. 5085
- Ramírez, M.C.¹ Toscano, R.A.² Arnason, J.³ Omar, S.⁴ Cerda-García-Rojas, C.M.⁵ Mata, R.⁶

79
- 0343550407
- and references therein
- (2000) Tetrahedron , vol.56 , pp. 1281
- Clyne, D.S.¹ Weiler, L.²

80
- 0033578846
- (1999) J. Org. Chem. , vol.64 , pp. 7224
- Taylor, R.E.¹ Zajicek, J.²

81
- 0025278271
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 450
- Keller, T.H.¹ Weiler, L.²

82
- 0034236754
- (2000) J. Chem. Soc., Perkin Trans. 2 , pp. 1477
- Kaisalo, L.¹ Koskimies, J.² Hase, T.³

83
- 0001834924
- (1990) Adv. Mol. Model. , vol.2 , pp. 65
- Gajewski, J.J.¹ Gilbert, K.E.² MacKelvey, J.³

84
- 84980966357
- (1966) Angew. Chem., Int. Ed. Engl. , vol.5 , pp. 1000
- Dale, J.¹

85
- 0033029390
- (1999) Synthesis , pp. 1034
- Kuksa, V.¹ Marshall, C.² Wardell, S.³ Kong Thoo Lin, P.⁴

86
- 0000968871
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 7858
- Keller, T.K.¹ Neeland, E.G.² Retting, S.³ Trotter, J.⁴ Weiler, L.⁵

87
- 0023620518
- (1987) J. Org. Chem. , vol.52 , pp. 4622
- Hauske, J.R.¹ Gaudliana, M.² Kostek, G.³ Shulte, G.⁴

88
- 4243489317
- (1963) Acta Crystallogr. , vol.16 , pp. 1075
- Fridrichson, J.¹ Mathieson, A.M.² Sutor, J.³

89
- 0034674252
- (2000) Angew. Chem., Int. Ed. , vol.39 , pp. 2054
- Hoffmann, R.W.¹

90
- 0026640040
- (1992) Angew. Chem., Int. Ed. Engl. , vol.31 , pp. 1124
- Hoffmann, R.W.¹

91
- 0000256093
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 1947
- Shannon, V.L.¹ Strauss, H.L.² Snyder, R.G.³ Elliger, C.A.⁴ Mattice, W.L.⁵

92
- 0000070468
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 8663
- Desper, J.M.¹ Gellman, S.H.² Wolf R.E., Jr.³ Cooper, S.R.⁴

93
- 0025144706
- See also ref 38
- (1990) Tetrahedron Lett. , vol.31 , pp. 6717
- Alder, R.W.¹ Maunder, C.M.² Orpen, A.G.³

94
- 0032931211
- (1999) Acc. Chem. Res. , vol.32 , pp. 127
- Bruice, T.C.¹ Lightstone, F.C.²

95
- 0029873183
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 2595
- Lightstone, F.C.¹ Bruice, T.C.²

96
- 0005781929
- (1921) Ber. , vol.54 , pp. 936
- Bergmann, M.¹ Brand, E.² Dreyer, F.³

97
- 33947090820
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 3824
- Menger, F.M.¹ Smith, J.H.²

98
- 0000433796
- (1967) Adv. Phys. Org. Chem. , vol.5 , pp. 237
- Johnson, S.L.¹

99
- 0016403522
- (1974) J. Org. Chem. , vol.39 , pp. 3841
- Kemp, D.S.¹ Choong, S.-L.H.² Pekaar, J.³

100
- 0001412115
- (1972) Can. J. Chem. , vol.50 , pp. 3405
- Deslongchamps, P.¹ Atlani, P.² Fréhel, D.³ Malaval, A.⁴

101
- 0001445223
- (1986) J. Org. Chem. , vol.51 , pp. 1829
- Kemp, D.S.¹ Galakatos, N.G.² Bowen, B.³ Tan, K.⁴

102
- 0001060641
- (1996) An. Quim. Int. Ed. , vol.92 , pp. 171
- Ivanov, P.M.¹ Pojarlieff, I.G.²

103
- 0005783961
- note

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.