SCOPUS 정보 검색 플랫폼

Journal of Organic Chemistry

Volumn 66, Issue 19, 2001, Pages 6305-6312

Efficient enantiomeric synthesis of pyrrolidine and piperidine alkaloids from tobacco

(6) Felpin, F X a Girard, S a Vo Thanh, G a Robins, R J a Villieras J a Lebreton, J a

a Centre National de la Recherche Scientifique (France)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOALKYLATION;

ALKYLATION; ORGANIC COMPOUNDS; TOBACCO;

SYNTHESIS (CHEMICAL);

ALDEHYDE; ALKALOID; ANABASINE; AZIDE; ESTER; NATURAL PRODUCT; NICOTINE; NORNICOTINE; PIPERIDINE; PYRIDINE DERIVATIVE; PYRROLIDINE DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; ENANTIOMER; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TOBACCO;

ALKALOIDS; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR CONFORMATION; PIPERIDINES; PLANTS, TOXIC; PYRROLIDINES; TOBACCO;

EID: 0035929390 PISSN: 00223263 EISSN: None Source Type: Journal
DOI: 10.1021/jo010386b Document Type: Article

Times cited : (139)

References (103)

1
- 0034676585
- (2000) Org. Lett. , vol.2 , pp. 3679-3681
- Watson, P.S.¹ Jiang, B.² Scott, B.³

2
- 0033612321
- (1999) J. Org. Chem. , vol.64 , pp. 4069-4078
- Xu, Y.-Z.¹ Choi, J.² Calaza, M.I.³ Turner, S.C.⁴ Rapoport, H.⁵

3
- 0033953747
- (2000) J. Org. Chem. , vol.65 , pp. 861-870
- Turner, S.C.¹ Zhai, H.² Rapoport, H.³

4
- 0033529950
- (1999) Tetrahedron Lett. , vol.40 , pp. 5915-5918
- Knight, D.W.¹ Salter, R.²

5
- 0033550231
- (1999) J. Org. Chem. , vol.64 , pp. 8594-8601
- Takahata, H.¹ Kubota, M.² Ikota, N.³

6
- 0034649174
- (2000) Tetrahedron Lett. , vol.41 , pp. 8157-8162
- Kumareswaran, R.¹ Balasubramanian, T.² Hassner, A.³

7
- 0034454809
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 4639-4643
- Agami, C.¹ Couty, F.² Evano, G.³

8
- 0033805359
- (2000) Synlett , pp. 1360-1362
- Eskici, M.¹ Gallagher, T.²

9
- 0033810418
- (2000) Synlett , pp. 1461-1463
- Cossy, J.¹ Willis, C.² Bellosta, V.³ Bouzbouz, S.⁴

10
- 0034720901
- (2000) Org. Lett. , vol.2 , pp. 2291-2293
- Lindström, S.¹ Ripa, L.² Halberg, A.³

11
- 0342514540
- (2000) Synlett , pp. 122-124
- Cossy, J.¹ Pévet, I.² Meyer, C.³

12
- 21844437339
- (1998) J. Chem. Soc., Chem. Commun. , pp. 633-640
- Bailey, P.D.¹ Millwood, P.A.² Smith, P.D.³

13
- 0033709712
- (2000) Synthesis , pp. 1781-1813
- Laschat, S.¹ Dickner, T.²

14
- 0020357264
- (1982) J. Am. Chem. Soc. , vol.104 , pp. 6440-6444
- Leete, E.¹ Mueller, M.E.²

15
- 0029046913
- (1995) Neuropharmacology , vol.34 , pp. 563-579
- Galzi, J.L.¹ Changeux, J.P.²

16
- 0033960085
- (2000) J. Pharmacol. Exp. Ther. , vol.292 , pp. 461-467
- Lloyd, G.K.¹ Williams, M.²

17
- 0031450275
- (1997) J. Med. Chem. , vol.40 , pp. 4169-4194
- Holladay, M.W.¹ Dart, M.J.² Lynch, J.K.³

18
- 0033577991
- (1999) J. Med. Chem. , vol.42 , pp. 2227-2234
- Latli, B.¹ D'Amour, K.² Casida, J.E.³

19
- 0034213308
- (2000) J. Med. Chem. , vol.43 , pp. 2217-2226
- Nielsen, S.F.¹ Nielsen, E.O.² Olsen, G.M.³ Liljefors, T.⁴ Peters, D.⁵

20
- 0034597576
- (2000) J. Med. Chem. , vol.43 , pp. 4045-4050
- Mullen, G.¹ Napier, J.² Balestra, M.³ DeCory, T.⁴ Hale, G.⁵ Macor, J.⁶ Mack, R.⁷ Loch III, J.⁸ Wu, E.⁹ Kover, A.¹⁰ Verhoest, P.¹¹ Sampognaro, A.¹² Phillips, E.¹³ Zhu, Y.¹⁴ Murray, R.¹⁵ Griffith, R.¹⁶ Blosser, J.¹⁷ Gurley, D.¹⁸ Machulskis, A.¹⁹ Zongrone, J.²⁰ Rosen, A.²¹ Gordon, J.²² more..

21
- 0002228660
- (2000) Chem. Eng. News , vol.78 , pp. 23-26
- Brennan, M.B.¹

22
- 0033547945
- and references there in
- (1999) Tetrahedron Lett. , vol.40 , pp. 1419-1422
- Malpass, J.R.¹ Cox, C.D.²

23
- 0029784854
- (1996) J. Med. Chem. , vol.39 , pp. 3235-3237
- Cosford, N.D.P.¹ Bleicher, L.² Herbaut, A.³ McCallum, J.S.⁴ Vernier, J.-M.⁵ Dawson, H.⁶ Whitten, J.P.⁷ Adams, P.⁸ Chavez-Noriega, L.⁹ Correa, L.D.¹⁰ Crona, J.H.¹¹ Mahaffy, L.S.¹² Menzaghi, F.¹³ Rao, T.S.¹⁴ Reid, R.¹⁵ Sacaan, A.I.¹⁶ Santori, E.¹⁷ Stauderman, K.A.¹⁸ Whelan, K.¹⁹ Lloyd, G.K.²⁰ McDonald, I.A.²¹ more..

24
- 0028575501
- (1994) J. Med. Chem. , vol.37 , pp. 4455-4463
- Garvey, D.S.¹ Wasicak, J.T.² Elliott, R.L.³ Lebold, S.A.⁴ Hettinger, A.-M.⁵ Carrera, G.M.⁶ Lin, N.-H.⁷ He, Y.⁸ Holladay, M.W.⁹ Anderson, D.J.¹⁰ Cadman, E.D.¹¹ Raszkiewicz, J.L.¹² Sullivan, J.P.¹³ Arneric, S.P.¹⁴

25
- 0028967687
- (1995) Eur. J. Pharmacol. , vol.276 , pp. 195-199
- Dwoski, L.P.¹ Teng, L.² Buxton, S.T.³ Ravard, A.⁴ Deo, N.⁵ Crooks, P.A.⁶

26
- 0003616826
- U. S. Patent 7,741,802, 1998
- Rem, W.R.¹ Zoltewicz, J.A.² Meyer, E.M.³ Prokal-Tatral, K.⁴

27
- 4243504880
- (1998) Chem. Abstr. , vol.128

28
- 0000025662
- (1996) Med. Chem. Res. , pp. 562-570
- Schneider, F.H.¹ Olsson, T.²

29
- 0018372681
- (1979) J. Med. Chem. , vol.22 , pp. 174-177
- Aceto, M.D.¹ Martin, B.R.² Uwaydah, I.M.³ May, E.L.⁴ Harris, L.S.⁵ Izazola-Conde, C.⁶ Deway, W.L.⁷ Bradshaw, T.J.⁸ Vincek, W.C.⁹

30
- 0033615783
- (1999) Tetrahedron Lett. , vol.40 , pp. 7847-7850
- Loh, T.-P.¹ Zhou, J.-R.² Li, X.-R.³ Sim, K.-Y.⁴

31
- 0032944904
- (1999) Chirality , vol.11 , pp. 316-318
- Swango, J.H.¹ Bhatti, B.S.² Quershi, M.M.³ Crooks, P.A.⁴

32
- 0000457970
- (1997) Pharm. Res. , vol.14 , pp. 695
- Swango, J.H.¹ Quershi, M.M.² Crooks, P.A.³

33
- 0020053582
- (1982) J. Org. Chem. , vol.47 , pp. 1069-1073
- Chavdarian, C.G.¹ Sanders, E.B.² Bassfield, R.L.³

34
- 0024447486
- (1989) J. Org. Chem. , vol.54 , pp. 4261-4263
- Pfrengle, W.¹ Kunz, H.²

35
- 0027392950
- (1993) Tetrahedron , vol.49 , pp. 1749-1760
- Hattori, K.¹ Yamamoto, H.²

36
- 0032479484
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2201-2205
- Balasubramanian, T.¹ Hassner, A.²

37
- 37049078529
- (1989) J. Chem. Soc., Chem. Commun. , pp. 1185-1187
- Mehmandoust, M.¹ Marazano, C.² Das, B.C.³

38
- 0035118962
- (2001) Eur. J. Org. Chem. , pp. 975-986
- Barco, A.¹ Benetti, S.² De Risi, C.³ Marchetti, P.⁴ Pollini, G.P.⁵ Zanirato, V.⁶

39
- 0032476114
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 3331-3352
- Yurovskaya, M.A.¹ Karchava, A.²

40
- 37049097825
- (1983) J. Chem. Soc., Perkin Trans. 1 , pp. 265-270
- Yamada, K.¹ Takeda, M.² Iwakuma, T.³

41
- 0000910778
- (1994) J. Am. Chem. Soc. , vol.116 , pp. 8952-8965
- Willoughby, C.A.¹ Buchwald, S.L.²

42
- 0032549047
- (1998) J. Org. Chem. , vol.63 , pp. 1109-1118
- Bleicher, L.S.¹ Cosford, N.D.P.² Herbaut, A.³ McCallum, J.S.⁴ McDonald, I.A.⁵

43
- 0033067090
- (1999) J. Org. Chem. , vol.64 , pp. 5299-5300
- Bleicher, L.S.¹ Cosford, N.D.P.²

44
- 0034715995
- (2000) Tetrahedron Lett. , vol.41 , pp. 9245-9249
- Girard, S.¹ Robins, R.J.² Villiéras, J.³ Lebreton, J.⁴

45
- 0033693609
- (2000) Synlett , pp. 1646-1648
- Felpin, F.-X.¹ Vo-Thanh, G.² Robins, R.J.³ Villiéras, J.⁴ Lebreton, J.⁵

46
- 58149324024
- and literature cited there in
- (1995) Bull. Soc. Chim. Fr. , vol.132 , pp. 1003-1008
- Carboni, B.¹ Vaultier, M.²

47
- 0000007391
- (1998) J. Organometallic Chem. , vol.567 , pp. 6614-6617
- Salmon, A.¹ Carboni, B.²

48
- 0029997094
- (1996) Tetrahedron Lett. , vol.37 , pp. 4091-4094
- Waid, P.P.¹ Flynn, G.A.² Huber Sabol, J.S.³

49
- 0023619369
- (1987) J. Am. Chem. Soc. , vol.109 , pp. 7151-7157
- Evans, D.A.¹ Weber, A.E.²

50
- 0001811974
- (1999) Aldrichimica Acta , vol.32 , pp. 75-89
- Phillips, A.J.¹ Abell, A.D.²

51
- 0032580376
- (1998) Tetrahedron , vol.54 , pp. 4413-4450
- Grubbs, R.H.¹ Chang, S.²

52
- 0038644039
- (2000) J. Org. Chem. , vol.65 , pp. 1738-1742
- Fürstner, A.¹ Thiel, O.R.²

53
- 0033606861
- (1999) Org. Lett. , vol.1 , pp. 615-617
- Cook, G.R.¹ Shanker, P.S.² Peterson, S.L.³

54
- 0034697496
- (2000) Tetrahedron Lett. , vol.41 , pp. 3927-3930
- Kigoshi, H.¹ Suzuki, Y.² Aoki, K.³ Uemura, D.⁴

55
- 0034681742
- (2000) Tetrahedron Lett. , vol.41 , pp. 2027-2029
- Wallace, D.J.¹ Cowden, C.J.² Kennedy, D.J.³ Ashwood, M.S.⁴ Cottrell, I.F.⁵ Dolling, U.-H.⁶

56
- 0032482518
- (1998) Tetrahedron Lett. , vol.39 , pp. 4139-4142
- Grigg, R.¹ Sridharan, V.² York, M.³

57
- 0000772326
- (2000) Org. Lett. , vol.2 , pp. 3971-3974
- Voigtmann, U.¹ Blechert, S.²

58
- 0034619119
- (2000) Tetrahedron Lett. , vol.41 , pp. 7843-7846
- Maldaner, A.O.¹ Pilli, R.A.²

59
- 0001646391
- (1991) J. Org. Chem. , vol.56 , pp. 401-404
- Racherla, U.S.¹ Brown, H.C.²

60
- 0001671926
- (1992) J. Org. Chem. , vol.57 , pp. 6614-6617
- Racherla, U.S.¹ Liao, Y.² Brown, H.C.³

61
- 33845374534
- (1986) J. Org. Chem. , vol.51 , pp. 432-439
- Jadhav, P.K.¹ Bhat, K.S.² Perumal, T.³ Brown, H.C.⁴

62
- 0003606882
- note

63
- 0027393923
- (1993) Tetrahedron Lett. , vol.34 , pp. 785-788
- Quallich, G.J.¹ Woodall, T.M.²

64
- 0002636206
- (1997) Synlett , pp. 273-274
- Masui, M.¹ Shioiri, T.²

65
- 0032568272
- (1998) Tetrahedron Lett. , vol.39 , pp. 1759-1762
- Chataigner, I.¹ Lebreton, J.² Durand, D.³ Guingant, A.⁴ Villiéras, J.⁵

66
- 0003608380
- note

67
- 0030570857
- (1996) Tetrahedron Lett. , vol.37 , pp. 5675-5678
- Corey, E.J.¹ Helal, C.J.²

68
- 0032572845
- (1998) Tetrahedron , vol.54 , pp. 10317-10328
- Lutz, C.¹ Graf, C.-D.² Knochel, P.³

69
- 33644528891
- (1983) J. Org. Chem. , vol.48 , pp. 4155-4156
- Dess, D.B.¹ Martin, J.C.²

70
- 33751158088
- (1994) J. Org. Chem. , vol.59 , pp. 7549-7552
- Meyer, S.D.¹ Schreiber, S.L.²

71
- 0026663693
- and references there in
- (1992) Synthesis , pp. 605-617
- Singh, V.K.¹

72
- 33845377255
- (1985) J. Am. Chem. Soc. , vol.107 , pp. 4513-4519
- Allen, A.D.¹ Kanagasabapathy, V.M.² Tidwell, T.T.³

73
- 33845469353
- (1984) J. Am. Chem. Soc. , vol.106 , pp. 1383-1396
- Richard, J.P.¹ Jencks, W.P.²

74
- 33947294347
- (1970) J. Org. Chem. , vol.35 , pp. 3195-3196
- Crossland, R.K.¹ Servis, K.L.²

75
- 0032909975
- (1999) Synlett , pp. 41-44
- Uenishi, J.¹ Takagi, T.² Ueno, T.³ Hiraoka, T.⁴ Yonemitsu, O.⁵ Tsukube, H.⁶

76
- 33751385202
- (1993) J. Org. Chem. , vol.58 , pp. 5886-5888
- Thompson, A.S.¹ Humphrey, G.R.² DeMarco, A.M.³ Mathre, D.J.⁴ Grabowski, E.J.J.⁵

77
- 0000865359
- (1977) Tetrahedron Lett. , pp. 1977-1980
- Lal, B.¹ Pramanik, B.N.² Manhas, M.S.³ Bose, A.K.⁴

78
- 0342647335
- (2000) Tetrahedron Lett. , vol.41 , pp. 5915-5918
- Lee, E.¹ Kim, S.K.² Kim, J.Y.³ Lim, J.⁴

79
- 0003721502
- note

80
- 0033550231
- (1999) J. Org. Chem. , vol.64 , pp. 8594-8601
- Takahata, H.¹ Kubota, M.² Ikota, N.³

81
- 0000367997
- (1990) Tetrahedron , vol.46 , pp. 587-594
- Bartra, M.¹ Romea, P.² Urpi, F.³ Vilarrasa, J.⁴

82
- 84988109905
- (1994) Synlett , pp. 137-140
- Lebreton, J.¹ Waldner, A.² Leseuer, C.³ De Mesmaeker, A.⁴

83
- 0001402361
- (1975) Synthesis , pp. 590-591
- Corey, E.J.¹ Nicolaou, K.C.² Balanson, R.D.³ Machida, Y.⁴

84
- 0003650792
- note

85
- 0033593493
- (1999) J. Org. Chem. , vol.64 , pp. 498-506
- Falb, E.¹ Bechor, Y.² Nudelman, A.³ Hassner, A.⁴ Albeck, A.⁵ Gottlieb, H.E.⁶

86
- 0000336605
- (1995) J. Org. Chem. , vol.60 , pp. 3980-3992
- Kise, N.¹ Oike, H.² Okazaki, E.³ Yoshimoto, M.⁴ Shono, T.⁵

87
- 0001215981
- (1999) Synlett , pp. 1749-1750
- Ling Ng, P.¹ Lambert, J.N.²

88
- 0032732493
- (1999) Synlett , pp. 1907-1910
- Raatz, D.¹ Innertsberger, C.² Reiser, O.³

89
- 78249281266
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 9856-9857
- Fu, G.C.¹ Nguyen, S.B.T.² Grubbs, R.B.³

90
- 0034697538
- (2000) Tetrahedron Lett. , vol.41 , pp. 3967-3970
- Evans, P.¹ Grigg, R.² York, M.³

91
- 0032482518
- (1998) Tetrahedron Lett. , vol.39 , pp. 4139-4142
- Grigg, R.¹ Sridharan, V.² York, M.³

92
- 0003683378
- note

93
- 0001294788
- (1982) J. Org. Chem. , vol.57 , pp. 3264-3265
- Hattori, K.¹ Yamamoto, H.²

94
- 0001531666
- (1998) J. Org. Chem. , vol.63 , pp. 5680-5683
- Haddad, M.¹ Imogaï, H.² Larchevêque, M.³

95
- 0000286496
- (1983) J. Am. Chem. Soc. , vol.105 , pp. 7640-7643
- Sanchez, I.H.¹ Lopez, F.J.² Soria, J.J.³ Larraza, M.I.⁴ Flores, H.J.⁵

96
- 0003616836
- (1959) Arch. Biochem. Biophys. , vol.80 , pp. 258-267
- Wada, E.¹ Kisaki, T.² Ihida, M.³

97
- 0028859125
- (1995) Tetrahedron , vol.51 , pp. 959-974
- Vazquez-Tato, M.P.¹ Seijas, J.A.² Fleet, G.W.J.³ Mathews, C.J.⁴ Hemmings, P.R.⁵ Brown, D.⁶

98
- 0031171037
- (1997) Can. J. Chem. , vol.75 , pp. 616-620
- Yang, C.-M.¹ Tanner, D.D.²

99
- 0000964167
- (1965) J. Org. Chem. , vol.30 , pp. 2769-2772
- Quan, P.M.¹ Karns, T.K.B.² Quin, L.D.³

100
- 0000310629
- (1983) Tetrahedron Lett. , vol.24 , pp. 1937-1940
- Alberici, G.F.¹ Andrieux, J.² Adam, G.³ Plat, M.M.⁴

101
- 0003680580
- note

102
- 85171870639
- (1937) Ber. Dtsch. Chem. Ges. , vol.70 , pp. 2450-2454
- Spath, E.¹ Kesztler, F.²

103
- 0344743411
- (1967) J. Organomet. Chem. , pp. 165-168
- Watson, S.C.¹ Eastham, J.F.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.