SCOPUS 정보 검색 플랫폼

Journal of Organic Chemistry

Volumn 66, Issue 9, 2001, Pages 3119-3128

Application of furanyl carbamate cycloadditions toward the synthesis of hexahydroindolinone alkaloids

(5) Padwa, A a Brodney, M A a Dimitroff, M a Liu, B a Wu, T a

a EMORY UNIVERSITY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

RING OPENINGS;

ADDITION REACTIONS; ESTERS; KETONES; REDUCTION;

SYNTHESIS (CHEMICAL);

CARBAMIC ACID DERIVATIVE; FURAN DERIVATIVE; HEXAHYDROINDOLINONE DERIVATIVE; INDOLIZIDINE ALKALOID; N [(2 METHYL 2 CYCLOPENTENYL)METHYL] N (4 ISOPROPYLFURAN 2 YL) CARBAMIC ACID; NITROGEN; TERT BUTYL METHYL ETHER; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; CYCLIZATION; ISOMERISM; MOLECULAR INTERACTION; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

ALKALOIDS; CARBAMATES; CYCLIZATION; INDOLES; MEMBRANES, ARTIFICIAL; PLANTS, MEDICINAL;

EID: 0035804964 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo010020z Document Type: Article

Times cited : (67)

References (94)

1
- 85007276529
- Rodrigo, R. G. A., Ed.; Academic Press: New York
- (1981) The Alkaloids , vol.19 , pp. 1-80
- Jeffs, P.W.¹

2
- 77957033352
- Brossi, A., Ed.; Academic Press: New York
- (1987) The Alkaloids , vol.30 , pp. 251-376
- Martin, S.F.¹

3
- 0000792906
- Cordell, G. A., Ed.; Academic Press: New York
- (1987) The Alkaloids , vol.51 , pp. 323
- Hoshino, O.¹

4
- 0034658826
- (2000) Org. Lett. , vol.2 , pp. 1673
- Rigby, J.H.¹ Dong, W.²

5
- 0032480928
- (1998) Tetrahedron Lett. , vol.39 , pp. 8979
- Dalko, P.I.¹ Brun, V.² Langlois, Y.³

6
- 0030980780
- (1997) J. Org. Chem. , vol.62 , pp. 3263
- Mori, M.¹ Kuroda, S.² Zhang, C.S.³ Sato, Y.⁴

7
- 0030974560
- (1997) J. Org. Chem. , vol.62 , pp. 1675
- Denmark, S.E.¹ Marcin, L.R.²

8
- 0031956797
- (1998) Nat. Prod. Rep. , vol.15 , pp. 107
- Lewis, J.R.¹

9
- 0034719244
- (2000) Org. Lett. , vol.2 , pp. 99
- Baldwin, S.W.¹ Debenham, J.S.²

10
- 0028096843
- (1994) J. Org. Chem. , vol.59 , pp. 5662
- Pearson, W.H.¹ Postich, M.J.²

11
- 0024595640
- (1989) Tetrahedron Lett. , vol.30 , pp. 647
- Overman, L.E.¹ Wild, H.²

12
- 0003544680
- (1989) J. Chem. Soc., Chem. Commun. , vol.1767
- Ishibashi, H.¹ Nakatani, H.² Iwami, S.³ Sato, T.⁴ Nakamura, N.⁵ Ikeda, M.⁶

13
- 0001138874
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 7781
- Hendrickson, J.B.¹ Bogard, T.L.² Fisch, M.E.³ Grossert, S.⁴ Yoshimura, N.⁵

14
- 0003624939
- (1972) Tetrahedron Lett. , vol.3153
- Tsuda, Y.¹ Ukai, A.² Isobe, K.³

15
- 33845553216
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 7591
- Danishefsky, S.¹ Morris, J.² Mullen, G.³ Gamill, R.⁴

16
- 0000560442
- (1983) J. Org. Chem. , vol.48 , pp. 2300
- White, J.D.¹ Chong, W.K.M.² Thirring, K.³

17
- 0023267914
- (1987) J. Org. Chem. , vol.52 , pp. 1962
- Martin, S.F.¹ Davidsen, S.K.² Puckette, T.A.³

18
- 0021749963
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 6431
- Martin, S.F.¹ Davidsen, S.K.²

19
- 0025180589
- (1990) J. Am. Chem. Soc. , vol.112 , pp. 6959
- Abelman, M.M.¹ Overman, L.E.² Tran, V.D.³

20
- 0032557235
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 3664
- Rigby, J.H.¹ Cavezza, A.² Heeg, M.J.³

21
- 0027289151
- (1993) J. Org. Chem. , vol.58 , pp. 2360
- Ishibashi, H.¹ Uemura, N.² Nakatani, H.³ Okazaki, M.⁴ Sato, T.⁵ Nakamura, N.⁶ Ikeda, M.⁷

22
- 0001646515
- (1991) J. Org. Chem. , vol.56 , pp. 6546
- Baldwin, S.W.¹ Auge, J.² McPhail, A.T.³

23
- 0001092327
- (1998) J. Org. Chem. , vol.63 , pp. 7586
- Nishimata, T.¹ Mori, M.²

24
- 0000880225
- (1998) J. Org. Chem. , vol.63 , pp. 5304
- Padwa, A.¹ Brodney, M.A.² Dimitroff, M.³

25
- 0030845835
- (1997) Tetrahedron , vol.53 , pp. 14179
- Kappe, C.O.¹ Murphree, S.S.² Padwa, A.³

26
- 0001549912
- (1984) J. Org. Chem. , vol.49 , pp. 3427
- Sternbach, D.D.¹ Rossana, D.M.² Onon, K.D.³

27
- 0001318394
- (1989) J. Am. Chem. Soc. , vol.111 , pp. 5469
- Jung, M.E.¹ Gervay, J.²

28
- 0033603620
- (1999) J. Org. Chem. , vol.64 , pp. 4617
- Padwa, A.¹ Brodney, M.A.² Satake, K.³ Straub, C.S.⁴

29
- 33845374099
- (1986) Chem. Rev. , vol.86 , pp. 795
- Lipshutz, B.H.¹

30
- 0003552585
- (1990) Synlett. , vol.173
- Vogel, P.¹ Fattori, D.² Gasparini, F.³ Le Drian, C.⁴

31
- 84988070738
- (1990) Bull. Soc. Chim. Belg. , vol.99 , pp. 395
- Vogel, P.¹

32
- 0003600546
- (1993) Synlett. , vol.177
- Lautens, M.¹

33
- 0003552587
- (1991) Synlett. , vol.321
- Cox, P.J.¹ Simpkins, N.S.²

34
- 0001361685
- (1992) J. Org. Chem. , vol.57 , pp. 2076
- Bimwala, R.M.¹ Vogel, P.²

35
- 0000647003
- (1960) Naturwissenschaften , vol.47 , pp. 231
- Popelak, A.¹ Lettenbaur, G.² Haak, E.³ Springer, H.⁴

36
- 0003613791
- (1968) Tetrahedron Lett. , vol.5445
- Oh-Ishi, T.¹ Kugita, H.²

37
- 0000777403
- (1969) J. Am. Chem. Soc. , vol.91 , pp. 3831
- Jeffs, P.W.¹ Hawks, R.L.² Farrier, D.S.³

38
- 0003521591
- (1977) J. Chem. Soc., Perkin Trans. 2 , vol.1098
- Capps, T.M.¹ Hargrave, K.D.² Jeffs, P.W.³ McPhail, A.T.⁴

39
- 85008532925
- (1979) Chem. Pharm. Bull. , vol.18 , pp. 291
- Ohishi, T.¹ Kugita, H.²

40
- 0003586036
- (1985) J. Chem. Soc., Chem. Commun. , vol.518
- Nagashima, H.¹ Ken-Ichi, A.² Wakamatsu, H.³ Itoh, K.⁴

41
- 0026536264
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 1329
- Pearson, W.H.¹ Szura, D.P.² Postich, M.J.³

42
- 0033601284
- (1999) J. Org. Chem. , vol.64 , pp. 9625
- Iwamatsu, S.¹ Matsubara, K.² Nagashima, H.³

43
- 0023690543
- (1988) J. Am. Chem. Soc. , vol.110 , pp. 4831
- Winkler, J.D.¹ Muller, C.L.² Scott, R.D.³

44
- 0001251039
- (1985) J. Org. Chem. , vol.50 , pp. 2386
- Cannizzo, L.F.¹ Grubbs, R.H.²

45
- 0003725829
- (1993) Synthesis , vol.1151
- Cannon, J.G.¹ Kirschbaum, K.S.²

46
- 33744887407
- (1983) Tetrahedron Lett. , vol.24 , pp. 4249
- Ohnuma, T.¹ Tabe, M.² Shiiya, K.³ Ban, Y.⁴

47
- 0003711060
- (1956) J. Am. Chem. Soc. , vol.78 , pp. 4180
- Wildman, W.C.¹

48
- 0032900708
- (1999) J. Org. Chem. , vol.64 , pp. 3595
- Padwa, A.¹ Brodney, M.A.² Liu, B.³ Satake, K.⁴ Wu, T.⁵

49
- 0003727716
- Diederich, F., Stang, P. J., Eds.; Wiley-VCH: Weinheim Germany, Chapter 2
- (1988) Metal-Catalyzed Cross-Coupling Reactions
- Suzuki, A.¹

50
- 0028829541
- (1995) Tetrahedron Lett. , vol.36 , pp. 7949
- Miller, R.A.¹ Humphrey, G.R.² Thompson, A.S.³

51
- 0003552589
- (1975) J. Chem. Soc., Perkin Trans. 1 , vol.1574
- Barton, D.H.R.¹ McCombie, S.W.²

52
- 0001094082
- (1981) J. Am. Chem. Soc. , vol.103 , pp. 3173
- Keck, G.E.¹ Webb, R.R.²

53
- 0003703812
- (1932) Pharm. Soc. Jpn. , vol.52 , pp. 1049
- Suzuki, H.¹ Keimatsu, I.² Ito, K.J.³

54
- 0000923989
- (1934) Pharm. Soc. Jpn. , vol.54 , pp. 802
- Suzuki, H.¹ Keimatsu, I.² Ito, K.J.³

55
- 0001655336
- (1935) Biol. Chem. , vol.111 , pp. 653
- Chen, K.K.¹ Chen, A.L.J.²

56
- 0014117017
- (1967) Chem. Rev. , vol.67 , pp. 441
- Porter, L.¹

57
- 0015511557
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 8278
- Yamada, K.¹ Suzuki, M.² Hayakawa, Y.³ Aoki, K.⁴ Nakamura, H.⁵ Nagase, H.⁶ Hirata, Y.⁷

58
- 0016373568
- (1974) Chem. Pharm. Bull. , vol.22 , pp. 349
- Inubushi, Y.¹ Kikushi, T.² Ibuka, T.³ Tanaka, T.⁴ Saji, I.⁵ Tokane, K.⁶

59
- 0016402493
- (1974) J. Am. Chem. Soc. , vol.96 , pp. 4332
- Kende, A.S.¹ Bentley, T.J.² Mader, R.A.³ Ridge, D.⁴

60
- 0018850711
- (1980) J. Am. Chem. Soc. , vol.102 , pp. 1390
- Roush, W.R.¹

61
- 0026749040
- (1992) J. Am. Chem. Soc. , vol.114 , pp. 4089
- Lee, C.H.¹ Westling, M.² Livinghouse, T.³ Williams, A.C.⁴

62
- 84985591654
- (1991) J. Am. Chem. Soc. , vol.113 , pp. 670
- Trost, B.M.¹ Tasker, A.S.² Rüther, G.³ Brandes, A.⁴

63
- 0024576972
- (1989) J. Org. Chem. , vol.54 , pp. 265
- Martin, S.F.¹ Li, W.²

64
- 0025973358
- (1991) J. Org. Chem. , vol.56 , pp. 642
- Martin, S.F.¹ Li, W.²

65
- 0027997696
- (1994) J. Org. Chem. , vol.59 , pp. 5633
- Mori, M.¹ Uesaka, N.² Shibasaki, M.³ Saitoh, F.⁴ Okamura, K.⁵ Date, T.⁶

66
- 0030900204
- (1997) J. Am. Chem. Soc. , vol.119 , pp. 4130
- Sha, C.K.¹ Chiu, R.T.² Yang, C.F.³ Yao, N.T.⁴ Tseng, W.H.⁵ Liao, F.L.⁶ Wang, S.L.⁷

67
- 0033618104
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 6072
- Cassayre, J.¹ Zard, S.Z.²

68
- 0003702837
- (1970) Tetrahedron Lett. , vol.4859
- Yamamoto, K.¹ Kawasaki, I.² Kaneko, T.³

69
- 0001094702
- (1975) J. Am. Chem. Soc. , vol.97 , pp. 6282
- Bosch, R.F.¹ Evans, A.J.² Wade, J.³

70
- 0017372091
- (1977) J. Am. Chem. Soc. , vol.99 , pp. 1612
- Bosch, R.F.¹ Evans, A.J.² Wade, J.³

71
- 0000105868
- (1975) J. Org. Chem. , vol.40 , pp. 2165
- Brattesani, D.N.¹ Heathcock, C.H.²

72
- 0001243886
- (1985) J. Org. Chem. , vol.50 , pp. 4135
- Conolly, P.J.¹ Heathcock, C.H.²

73
- 0003521593
- (1992) Chem. Lett. , vol.443
- Takano, S.¹ Inomata, K.² Ogasawara, K.³

74
- 0032580376
- (1998) Tetrahedron , vol.54 , pp. 4413
- Grubbs, R.H.¹ Chang, S.²

75
- 0000755941
- (1997) Angew. Chem., Int. Ed. Engl. , vol.36 , pp. 2037
- Schuster, M.¹ Blechert, S.²

76
- 0032924763
- (1999) Curr. Org. Chem. , vol.3 , pp. 211
- Wright, D.L.¹

77
- 33746236970
- (1995) Angew. Chem., Int. Ed. Engl. , vol.34 , pp. 2039
- Schwab, P.¹ France, M.B.² Ziller, J.W.³ Grubbs, R.H.⁴ Ziller, J.⁵

78
- 0028017556
- (1994) Tetrahedron: Asymmetry , vol.5 , pp. 1411
- Woo, S.¹ Keay, B.A.²

79
- 0025995752
- (1991) Tetrahedron Lett. , vol.32 , pp. 6477
- Rogers, C.¹ Keay, B.A.²

80
- 0003669515
- (1991) Synlett. , vol.353
- Rogers, C.¹ Keay, B.A.²

81
- 0000780402
- (1992) Can. J. Chem. , vol.70 , pp. 2929
- Rogers, C.¹ Keay, B.A.²

82
- 0343758072
- (1979) Synth. Commun. , vol.9 , pp. 771
- De Clercq, P.J.¹ Van Royen, L.A.²

83
- 0000541423
- (1984) Bull. Soc. Chim. Belg. , vol.93 , pp. 1019
- Van Royen, L.A.¹ Mijngheer, R.² De Clercq, P.J.³

84
- 0000496674
- (1987) J. Org. Chem. , vol.52 , pp. 564
- Fischer, K.¹ Hünig, S.²

85
- 0003532168
- (1973) J. Chem. Soc., Perkin Trans. 1 , vol.2327
- Chadwick, D.J.¹ Chambers, J.² Hargraves, H.E.³ Meakins, G.D.⁴ Snowden, R.L.⁵

86
- 0015520853
- (1972) J. Am. Chem. Soc. , vol.94 , pp. 6203
- Shioiri, T.¹ Ninomiya, K.² Yamada, S.³

87
- 0034609701
- (2000) Org. Lett. , vol.2 , pp. 3233
- Padwa, A.¹ Dimitroff, M.² Liu, B.³

88
- 0003622802
- note

89
- 84915949969
- (1943) Chem. Ber. , vol.76 , pp. 895
- Kratzl, E.¹

90
- 0029402785
- (1995) J. Am. Chem. Soc. , vol.117 , pp. 11695
- Barton, T.J.¹ Lin, J.² Ijadi-Maghsoodi, S.³ Power, M.D.⁴ Zhang, X.⁵

91
- 0025973358
- (1991) J. Org. Chem. , vol.56 , pp. 642
- Martin, S.F.¹ Li, W.²

92
- 0001326748
- (1933) J. Am. Chem. Soc. , vol.55 , pp. 4197
- Gilman, H.¹ Calloway, N.O.²

93
- 0003727718
- (1935) J. Am. Chem. Soc. , vol.57 , pp. 906
- Gilman, H.¹ Calloway, N.O.²

94
- 0001060724
- (1976) J. Org. Chem. , vol.41 , pp. 2835
- Divald, S.¹ Chun, M.C.² Joullie, M.M.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.