SCOPUS 정보 검색 플랫폼 - 논문 보기

메뉴 건너뛰기

Organic Letters

Volumn 7, Issue 24, 2005, Pages 5401-5404

Electrophilic activation of lactams with Tf2O and pyridine: Expedient synthesis of (±)-tetraponerine T4

(3) Charette, André B a Mathieu, Simon a Martel, Jonathan a

a UNIVERSITÉ DE MONTRÉAL (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FUSED HETEROCYCLIC RINGS; LACTAM; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE; TETRAPONERINE T4;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

CATALYSIS; HETEROCYCLIC COMPOUNDS, 3-RING; LACTAMS; MOLECULAR STRUCTURE; PYRIDINES; PYRIDINIUM COMPOUNDS; STEREOISOMERISM;

EID: 28844505658 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol052069n Document Type: Article

Times cited : (66)

References (59)

1
- 0023919077
- (a) Merlin, P.; Braekman, J. C.; Daloze, D.; Pasteels, J. M. J. Chem. Ecol. 1988, 14, 517-527.
- (1988) J. Chem. Ecol. , vol.14 , pp. 517-527
- Merlin, P.¹ Braekman, J.C.² Daloze, D.³ Pasteels, J.M.⁴

2
- 0008176367
- (b) Braekman, J. C.; Daloze, D.; Pasteels, J. M.; Vanhecke, P.; Declercq, J. P.; Sinnwell, V.; Franke, W. Z. Naturforsch. 1987, 42c, 627-630.
- (1987) Z. Naturforsch. , vol.42 C , pp. 627-630
- Braekman, J.C.¹ Daloze, D.² Pasteels, J.M.³ Vanhecke, P.⁴ Declercq, J.P.⁵ Sinnwell, V.⁶ Franke, W.⁷

3
- 4043175420
- (a) Kim, J. T.; Butt, J.; Gevorgyan, V. J. Org. Chem. 2004, 69, 5638-5645.
- (2004) J. Org. Chem. , vol.69 , pp. 5638-5645
- Kim, J.T.¹ Butt, J.² Gevorgyan, V.³

4
- 0347812063
- (b) Kim, J. T.; Gevorgyan, V. Org. Lett. 2002, 4, 4697-4699.
- (2002) Org. Lett. , vol.4 , pp. 4697-4699
- Kim, J.T.¹ Gevorgyan, V.²

5
- 0033550231
- (c) Takahata, H.; Kubota, M.; Ikota, N. J. Org. Chem. 1999, 64, 8594-8501.
- (1999) J. Org. Chem. , vol.64 , pp. 8594-18501
- Takahata, H.¹ Kubota, M.² Ikota, N.³

6
- 0001506850
- (d) Barluenga, J.; Tomás, M.; Kouznetsov, V.; Rubio, E. J. Org. Chem. 1994, 59, 9, 3699-3700.
- (1994) J. Org. Chem. , vol.59 , Issue.9 , pp. 3699-3700
- Barluenga, J.¹ Tomás, M.² Kouznetsov, V.³ Rubio, E.⁴

7
- 0025729061
- (e) Merlin, P.; Braekman, J. C.; Daloze, D. Tetrahedron 1991, 47, 3805-3816.
- (1991) Tetrahedron , vol.47 , pp. 3805-3816
- Merlin, P.¹ Braekman, J.C.² Daloze, D.³

8
- 0025279564
- (f) Jones, T. H. Tetrahedron Lett. 1990, 31, 4543-4544.
- (1990) Tetrahedron Lett. , vol.31 , pp. 4543-4544
- Jones, T.H.¹

9
- 28844452192
- (g) Jones, T. H. Tetrahedron Lett. 1990, 31, 1538-1541.
- (1990) Tetrahedron Lett. , vol.31 , pp. 1538-1541
- Jones, T.H.¹

10
- 28844483870
- (h) Merlin, P.; Braekman, J. C.; Daloze, D. Tetrahedron Lett. 1988, 29, 3805-3816.
- (1988) Tetrahedron Lett. , vol.29 , pp. 3805-3816
- Merlin, P.¹ Braekman, J.C.² Daloze, D.³

11
- 0034638362
- (a) Stragies, R.; Blechert, S. J. Am. Chem. Soc. 2000, 122, 9584-9591.
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 9584-9591
- Stragies, R.¹ Blechert, S.²

12
- 0033838114
- (b) Plehiers, M.; Heilporn, S.; Ekelmans, D.; Leclercq, S.; Sangermano, M.; Braekman, J. C.; Daloze, D. Can. J. Chem. 2000, 78, 1030-1034.
- (2000) Can. J. Chem. , vol.78 , pp. 1030-1034
- Plehiers, M.¹ Heilporn, S.² Ekelmans, D.³ Leclercq, S.⁴ Sangermano, M.⁵ Braekman, J.C.⁶ Daloze, D.⁷

13
- 0030037070
- (c) Yue, C.; Gauthier, I.; Royer, J.; Husson, H.-P. J. Org. Chem. 1996, 61, 4949-4954.
- (1996) J. Org. Chem. , vol.61 , pp. 4949-4954
- Yue, C.¹ Gauthier, I.² Royer, J.³ Husson, H.-P.⁴

14
- 0029087664
- (d) Devijver, C.; Macours, P.; Braekman, J. C.; Daloze, D.; Pasteels, J. M. Tetrahedron 1995, 51, 10913-10922.
- (1995) Tetrahedron , vol.51 , pp. 10913-10922
- Devijver, C.¹ Macours, P.² Braekman, J.C.³ Daloze, D.⁴ Pasteels, J.M.⁵

15
- 0028795083
- (e) Macours, P.; Braekman, J. C.; Daloze, D. Tetrahedron 1995, 51, 1415-1428.
- (1995) Tetrahedron , vol.51 , pp. 1415-1428
- Macours, P.¹ Braekman, J.C.² Daloze, D.³

16
- 0025272119
- (f) Yue, C. Y.; Royer, J.; Husson, H.-P. J. Org. Chem. 1990, 55, 1140-1141.
- (1990) J. Org. Chem. , vol.55 , pp. 1140-1141
- Yue, C.Y.¹ Royer, J.² Husson, H.-P.³

17
- 0007484259
- (a) Comins, D. L.; Brown, J. D. Tetrahedron Lett. 1986, 27, 2219-2222.
- (1986) Tetrahedron Lett. , vol.27 , pp. 2219-2222
- Comins, D.L.¹ Brown, J.D.²

18
- 0013557506
- (b) Courtois, G.; Al-arnaout, A.; Miginiac, L. Tetrahedron Lett. 1985, 26, 1027-1030.
- (1985) Tetrahedron Lett. , vol.26 , pp. 1027-1030
- Courtois, G.¹ Al-arnaout, A.² Miginiac, L.³

19
- 0013514478
- (c) Comins, D. L.; Brown, J. D. Tetrahedron Lett. 1984, 25, 3297-3300.
- (1984) Tetrahedron Lett. , vol.25 , pp. 3297-3300
- Comins, D.L.¹ Brown, J.D.²

20
- 0013556083
- See also for addition of silyl enol ethers: (d) Wada, M.; Nishihara, Y.; Akiba, K. Tetrahedron Lett. 1985, 26, 3267-3270.
- (1985) Tetrahedron Lett. , vol.26 , pp. 3267-3270
- Wada, M.¹ Nishihara, Y.² Akiba, K.³

21
- 0000766693
- (e) Akiba, K.; Iseki, Y.; Wada, M. Tetrahedron Lett. 1982, 23, 429-432.
- (1982) Tetrahedron Lett. , vol.23 , pp. 429-432
- Akiba, K.¹ Iseki, Y.² Wada, M.³

22
- 3543018504
- (a) Kuethe, J. T.; Comins, D. L. J. Org. Chem. 2004, 69, 5219-5231.
- (2004) J. Org. Chem. , vol.69 , pp. 5219-5231
- Kuethe, J.T.¹ Comins, D.L.²

23
- 0034704647
- (b) Kuethe, J. T.; Comins, D. L. Org. Lett. 2000, 2, 855-857.
- (2000) Org. Lett. , vol.2 , pp. 855-857
- Kuethe, J.T.¹ Comins, D.L.²

24
- 0033599533
- (c) Comins, D. L.; Kuethe, J. T.; Hong, H.; Lakner, F. J.; Concolino, T. E.; Rheingold, A. L. J. Am. Chem. Soc. 1999, 121, 2651-2652.
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 2651-2652
- Comins, D.L.¹ Kuethe, J.T.² Hong, H.³ Lakner, F.J.⁴ Concolino, T.E.⁵ Rheingold, A.L.⁶

25
- 0000073031
- (d) Comins, D. L.; Hong, H. J. Am. Chem. Soc. 1993, 115, 8851-8852.
- (1993) J. Am. Chem. Soc. , vol.115 , pp. 8851-8852
- Comins, D.L.¹ Hong, H.²

26
- 0027494184
- (e) Comins, D. L.; Hong, H. J. Org. Chem. 1993, 58, 5035-5036.
- (1993) J. Org. Chem. , vol.58 , pp. 5035-5036
- Comins, D.L.¹ Hong, H.²

27
- 0035684195
- Charette, A. B.; Grenon, M. Can. J. Chem. 2001, 79, 1694-1703.
- (2001) Can. J. Chem. , vol.79 , pp. 1694-1703
- Charette, A.B.¹ Grenon, M.²

28
- 0029856617
- (a) Barbara, G.; Battaglia, A.; Bruno, C.; Giorgianni, P.; Guerrini, A. J. Org. Chem. 1996, 61, 8480-8488.
- (1996) J. Org. Chem. , vol.61 , pp. 8480-8488
- Barbara, G.¹ Battaglia, A.² Bruno, C.³ Giorgianni, P.⁴ Guerrini, A.⁵

29
- 84985574411
- (b) Falmagne, J. B.; Escudero, J.; Taleb-Saharaoui, S.; Ghosez, L. Angew. Chem., Int. Ed. Engl. 1981, 20, 879-880.
- (1981) Angew. Chem., Int. Ed. Engl. , vol.20 , pp. 879-880
- Falmagne, J.B.¹ Escudero, J.² Taleb-Saharaoui, S.³ Ghosez, L.⁴

30
- 0345890132
- (a) Sisti, N. J.; Zeller, E.; Grierson, D. S.; Fowler, F. W. J. Org. Chem. 1997, 62, 2093-2097.
- (1997) J. Org. Chem. , vol.62 , pp. 2093-2097
- Sisti, N.J.¹ Zeller, E.² Grierson, D.S.³ Fowler, F.W.⁴

31
- 0027209127
- (b) Thomas, E. W. Synthesis 1993, 767-768.
- (1993) Synthesis , pp. 767-768
- Thomas, E.W.¹

32
- 84918218889
- (c) Sisti, N. J.; Fowler, F. W.; Grierson, D. S. Synlett 1991, 816-818.
- (1991) Synlett , pp. 816-818
- Sisti, N.J.¹ Fowler, F.W.² Grierson, D.S.³

33
- 0038675618
- (a) Thioamides, see: Charette, A. B.; Grenon, M. J. Org. Chem. 2003, 68, 5792-5794.
- (2003) J. Org. Chem. , vol.68 , pp. 5792-5794
- Charette, A.B.¹ Grenon, M.²

34
- 0032518886
- (b) Charette, A. B.; Chua, P. Tetrahedron Lett. 1998, 39, 245-248.
- (1998) Tetrahedron Lett. , vol.39 , pp. 245-248
- Charette, A.B.¹ Chua, P.²

35
- 0034635862
- (c) Amidines, see: Charette, A. B.; Grenon, M. Tetrahedron Lett. 2000, 41, 1677-1680.
- (2000) Tetrahedron Lett. , vol.41 , pp. 1677-1680
- Charette, A.B.¹ Grenon, M.²

36
- 0001004124
- (d) Thiazolines, see: Charette, A. B.; Chua, P. J. Org. Chem. 1998, 65, 908-909.
- (1998) J. Org. Chem. , vol.65 , pp. 908-909
- Charette, A.B.¹ Chua, P.²

37
- 0002474959
- (e) Esters, see: Charette, A. B.; Chua, P. Synlett 1998, 163-165.
- (1998) Synlett , pp. 163-165
- Charette, A.B.¹ Chua, P.²

38
- 0030668491
- (f) Cyclic ortho esters, see: Charette, A. B.; Chua, P. Tetrahedron Lett. 1997, 38, 8499-8502.
- (1997) Tetrahedron Lett. , vol.38 , pp. 8499-8502
- Charette, A.B.¹ Chua, P.²

39
- 4644242670
- (a) Mans, D. M.; Pearson, W. H. J. Org. Chem. 2004, 69, 6419-6426.
- (2004) J. Org. Chem. , vol.69 , pp. 6419-6426
- Mans, D.M.¹ Pearson, W.H.²

40
- 0034705460
- (b) Chacun-Lefèvre, L.; Joseph, B.; Mérour, J.-Y. Tetrahedron 2000, 56, 4491-4499.
- (2000) Tetrahedron , vol.56 , pp. 4491-4499
- Chacun-Lefèvre, L.¹ Joseph, B.² Mérour, J.-Y.³

41
- 0006327007
- (c) Nagai, S.; Kato, N.; Ueda, T.; Oda, N.; Sakakibara, J. Heterocycles 1986, 24, 907-912.
- (1986) Heterocycles , vol.24 , pp. 907-912
- Nagai, S.¹ Kato, N.² Ueda, T.³ Oda, N.⁴ Sakakibara, J.⁵

42
- 0001731781
- (d) Hendrickson, J. B.; Bergeron, R. Tetrahedron Lett. 1973, 46, 4607-4610.
- (1973) Tetrahedron Lett. , vol.46 , pp. 4607-4610
- Hendrickson, J.B.¹ Bergeron, R.²

43
- 18844404182
- (a) Kuhnert, N.; Clemens, I.; Walsh, R. Org. Biomol. Chem. 2005, 3, 1694-1701.
- (2005) Org. Biomol. Chem. , vol.3 , pp. 1694-1701
- Kuhnert, N.¹ Clemens, I.² Walsh, R.³

44
- 0013284522
- (b) Rashatasakhon, P.; Padwa, A. Org. Lett. 2003, 5, 189-191.
- (2003) Org. Lett. , vol.5 , pp. 189-191
- Rashatasakhon, P.¹ Padwa, A.²

45
- 0037419163
- (c) Padwa, A.; Crawford, K. R.; Rashatasakhon, P.; Rose, M. J. Org. Chem. 2003, 68, 2609-2617.
- (2003) J. Org. Chem. , vol.68 , pp. 2609-2617
- Padwa, A.¹ Crawford, K.R.² Rashatasakhon, P.³ Rose, M.⁴

46
- 0033006071
- (d) Vonhoff, S.; Vasella, A. Synth. Commun. 1999, 29, 551-560.
- (1999) Synth. Commun. , vol.29 , pp. 551-560
- Vonhoff, S.¹ Vasella, A.²

47
- 28844433130
- note
- See Supporting Information for detailed protocols and NMR monitoring of each reaction.

48
- 28844456624
- note
- Reaction of isolated 3b with EtMgBr in our standard conditions (see Table 2) gave dihydropyridine 8b in 91% yield.

49
- 28844432093
- note
- 2O to provide single crystals suitable for X-ray analysis.

50
- 0032831523
- and references therein
- For examples of related N-acylpyridinium salt isolation, see: (a) Wagner, R.; Wiebel, B.; Günther, W.; Görls, H.; Anders, E. Eur. J. Org. Chem. 1999, 2383-2390 and references therein.
- (1999) Eur. J. Org. Chem. , pp. 2383-2390
- Wagner, R.¹ Wiebel, B.² Günther, W.³ Görls, H.⁴ Anders, E.⁵

51
- 0028772916
- (b) Singh, P.; Comins, D. L.; Joseph, S. P. Acta Crystallogr. 1994, C50, 25-27.
- (1994) Acta Crystallogr. , vol.50 , pp. 25-27
- Singh, P.¹ Comins, D.L.² Joseph, S.P.³

52
- 0008016653
- (c) King, J. A.; Bryant, G. L. J. Org. Chem. 1992, 57, 5136-5139.
- (1992) J. Org. Chem. , vol.57 , pp. 5136-5139
- King, J.A.¹ Bryant, G.L.²

53
- 0003737657
- (d) Bryant, G. L.; King, J. A. Acta Crystallogr. 1992, C48, 2036-2039.
- (1992) Acta Crystallogr. , vol.C48 , pp. 2036-2039
- Bryant, G.L.¹ King, J.A.²

54
- 0035965734
- Charette, A. B.; Grenon, M.; Lemire, A.; Pourashraf, M.; Martel, J. J. Am. Chem. Soc. 2001, 123, 11829-11830.
- (2001) J. Am. Chem. Soc. , vol.123 , pp. 11829-11830
- Charette, A.B.¹ Grenon, M.² Lemire, A.³ Pourashraf, M.⁴ Martel, J.⁵

55
- 6444238793
- Lemire, A.; Grenon, M.; Pourashraf, M.; Charette, A. B. Org. Lett. 2004, 6, 3517-3520.
- (2004) Org. Lett. , vol.6 , pp. 3517-3520
- Lemire, A.¹ Grenon, M.² Pourashraf, M.³ Charette, A.B.⁴

56
- 15444361998
- Lemire, A.; Beaudoin, D.; Grenon, M.; Charette, A. B. J. Org. Chem. 2005, 70, 2368-2371.
- (2005) J. Org. Chem. , vol.70 , pp. 2368-2371
- Lemire, A.¹ Beaudoin, D.² Grenon, M.³ Charette, A.B.⁴

57
- 27644547805
- Lemire, A.; Charette, A. B. Org. Lett. 2005, 7, 2747-2750.
- (2005) Org. Lett. , vol.7 , pp. 2747-2750
- Lemire, A.¹ Charette, A.B.²

58
- 28844485146
- note
- 13C NMR.

59
- 28844464467
- note
- 19F NMR.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.