SCOPUS 정보 검색 플랫폼

Volumn 16, Issue 1, 2010, Pages 282-287

Protecting-group-free total synthesis of isoquinoline alkaloids by nickel-catalyzed annulation of o-halobenzaldimine with an alkyne as the key step

(2) Korivi, Rajendra Prasad a Cheng, Chien Hong a

a NATIONAL TSING HUA UNIVERSITY (Taiwan)

Author keywords

Alkaloids; Isoquinolines; Nickel; Ring closing reactions; Total synthesis

Indexed keywords

ALCOHOL GROUP; ALDEHYDE MOIETY; ALKALOIDS; IN-SITU OXIDATION; ISOQUINOLINES; OH GROUP; PHENANTHRIDINE; REGIO-SELECTIVE; RING-CLOSING REACTIONS; TOTAL SYNTHESIS;

ACETYLENE; ALDEHYDES; CYCLIZATION; NICKEL; NICKEL ALLOYS; OXIDATION;

SYNTHESIS (CHEMICAL);

ALKALOID; ALKYNE; HALOGENATED HYDROCARBON; IMINE; ISOQUINOLINE DERIVATIVE; NICKEL;

ARTICLE; CATALYSIS; CHEMISTRY; CYCLIZATION; OXIDATION REDUCTION REACTION; STEREOISOMERISM; STRUCTURE ACTIVITY RELATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

ALKALOIDS; ALKYNES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; CYCLIZATION; HYDROCARBONS, HALOGENATED; IMINES; ISOQUINOLINES; NICKEL; OXIDATION-REDUCTION; STEREOISOMERISM; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 73949084691 PISSN: 09476539 EISSN: 15213765 Source Type: Journal
DOI: 10.1002/chem.200902275 Document Type: Article

Times cited : (72)

References (64)

1
- 14644436385
- a) G. M. Cragg, D. J. Newman, Pure Appl. Chem. 2005, 77, 7-24;
- (2005) Pure Appl. Chem. , vol.77 , pp. 7-24
- Cragg, G.M.¹ Newman, D.J.²

2
- 7044281754
- b) L. F. Tietze, H. R Bell, S. Chandrasekhar, Angew. Chem. 2003, 115, 4128-4160;
- (2003) Angew. Chem. , vol.115 , pp. 4128-4160
- Tietze, L.F.¹ Bell, H.R.² Chandrasekhar, S.³

3
- 0141427680
- Angew. Chem. Int. Ed. 2003, 42, 3996-4028;
- (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 3996-4028

4
- 21444453119
- c) B. A. Posner, Curr. Opin. Drug Discovery Dev. 2005, 8, 487-494.
- (2005) Curr. Opin. Drug Discovery Dev. , vol.8 , pp. 487-494
- Posner, B.A.¹

5
- 73949158539
- US Patent, US 2005/0113399A1
- a) R. M. Scarborough, K. A. Kane-Maguire, C. K. Marlowe, M. S. Smyth, X. Zhang, US Patent, US 2005/0113399A1, 2005;
- (2005)
- Scarborough, R.M.¹ Kane-Maguire, K.A.² Marlowe, C.K.³ Smyth, M.S.⁴ Zhang, X.⁵

6
- 73949134694
- Int. Patent, WO 2006/067444A1
- b) N. I. Alun, P. K. Mark, B. P Allen, Int. Patent, WO 2006/067444A1, 2006;
- (2006)
- Alun, N.I.¹ Mark, P.K.² Allen, B.P.³

7
- 73949094948
- Int. Patent, WO 2007/149031A1
- c) M. Barrie, W. Paul, Int. Patent, WO 2007/149031A1, 2007;
- (2007)
- Barrie, M.¹ Paul, W.²

8
- 73949144183
- Int. Patent, WO 2004/108682A2
- d) L. J. Adams, Int. Patent, WO 2004/108682A2, 2004;
- (2004)
- Adams, L.J.¹

9
- 73949138498
- Int. Patent, WO 2008/037482A1
- e) B. Gerhard, T. Guider, U. Hentschel, F. Meyer, H. Moll, J. Morschhauser, D. V. A. Ponte-Sucre, W. Ziebuhr; A. Stich, R. Brun, W. E. G. Muller, V. Mudogu, Int. Patent, WO 2008/037482A1, 2008;
- (2008)
- Gerhard, B.¹ Guider, T.² Hentschel, U.³ Meyer, F.⁴ Moll, H.⁵ Morschhauser, J.⁶ Ponte-Sucre, D.V.A.⁷ Ziebuhr, W.⁸ Stich, A.⁹ Brun, R.¹⁰ Muller, W.E.G.¹¹ Mudogu, V.¹²

10
- 73949112972
- WO 2005/089294A2
- f) M. S. Cushman, A. S. Ioanoviciu, Y. G. Pommier, WO 2005/089294A2, 2005;
- (2005)
- Cushman, M.S.¹ Ioanoviciu, A.S.² Pommier, Y.G.³

11
- 73949136978
- N-laurylisoquinolinium bromide, hexadecamethylenediisoquinolium dichloride and quinapril are popular drug molecules.
- g) N-laurylisoquinolinium bromide, hexadecamethylenediisoquinolium dichloride and quinapril are popular drug molecules.

12
- 0021362527
- a) B. D. Krane, M. O. Fagbule, M. Shamma, J. Nat. Prod. 1984, 47, 1-43;
- (1984) J. Nat. Prod. , vol.47 , pp. 1-43
- Krane, B.D.¹ Fagbule, M.O.² Shamma, M.³

13
- 0026903955
- b) K. W. Bentley, Nat. Prod. Rep. 1992, 9, 365-391;
- (1992) Nat. Prod. Rep. , vol.9 , pp. 365-391
- Bentley, K.W.¹

14
- 0021478581
- c) K. W. Bentley, Nat. Prod. Rep. 1984, 1, 355-370;
- (1984) Nat. Prod. Rep. , vol.1 , pp. 355-370
- Bentley, K.W.¹

15
- 36348946829
- d) J. Fotie, D. S. Bohle, M. Olivier, M. A. Gomez, S. Nzimiro, J. Nat. Prod. 2007, 70, 1650-1653;
- (2007) J. Nat. Prod. , vol.70 , pp. 1650-1653
- Fotie, J.¹ Bohle, D.S.² Olivier, M.³ Gomez, M.A.⁴ Nzimiro, S.⁵

16
- 0025090928
- e) T. Tanahashi, M. H. Zenk, J. Nat. Prod. 1990, 53, 579-586.
- (1990) J. Nat. Prod. , vol.53 , pp. 579-586
- Tanahashi, T.¹ Zenk, M.H.²

17
- 0005484583
- a) H. R. Arthur, W. H. Hui, Y. L. Ng, J. Chem. Soc. 1959, 4007-4009;
- (1959) J. Chem. Soc. , pp. 4007-4009
- Arthur, H.R.¹ Hui, W.H.² Ng, Y.L.³

18
- 34247356943
- b) S.-Q. Wang, G.-Q. Wang, B.-K. Huang, Q.-Y. Zhang, L.-P. Qin, Chem. Nat. Compd. 2007, 43, 100-102;
- (2007) Chem. Nat. Compd. , vol.43 , pp. 100-102
- Wang, S.-Q.¹ Wang, G.-Q.² Huang, B.-K.³ Zhang, Q.-Y.⁴ Qin, L.-P.⁵

19
- 33749587618
- c) J. Hu, W.-D. Zhang, R.-H. Liu, C. Zhang, Y.-H. Shen, H.-L. Li, M.-J. Liang, X.-K. Xu, Chem. Biodiversity 2006, 3, 990-995.
- (2006) Chem. Biodiversity , vol.3 , pp. 990-995
- Hu, J.¹ Zhang, W.-D.² Liu, R.-H.³ Zhang, C.⁴ Shen, Y.-H.⁵ Li, H.-L.⁶ Liang, M.-J.⁷ Xu, X.-K.⁸

20
- 0031454923
- a) N. F. D. Moura, H. B. Ribeiro, E. C. S. Machado, E. M. Ethur, N. Zanatta, A. F. Morel, Phytochemistry 1997, 46, 8, 1443-1446;
- (1997) Phytochemistry , vol.46 , Issue.8 , pp. 1443-1446
- Moura, N.F.D.¹ Ribeiro, H.B.² Machado, E.C.S.³ Ethur, E.M.⁴ Zanatta, N.⁵ Morel, A.F.⁶

21
- 0002745795
- b) H. R. Arthur, W. H. Hui, Y. L. Ng, J. Chem. Soc. 1959, 1840-1845;
- (1959) J. Chem. Soc. , pp. 1840-1845
- Arthur, H.R.¹ Hui, W.H.² Ng, Y.L.³

22
- 0023631525
- c) M. E. Wall, M. C. Wani, H. Taylor, J. Nat. Prod. 1987, 50, 1095-1099;
- (1987) J. Nat. Prod. , vol.50 , pp. 1095-1099
- Wall, M.E.¹ Wani, M.C.² Taylor, H.³

23
- 0030757496
- d) C.-T. Chang, S.-C. Doong, I.-L. Tsai, I.-S. Chen, Phytochemistry 1997, 45, 7, 1419-1422.
- (1997) Phytochemistry , vol.45 , Issue.7 , pp. 1419-1422
- Chang, C.-T.¹ Doong, S.-C.² Tsai, I.-L.³ Chen, I.-S.⁴

24
- 30644477735
- a) M. Mizuno, H. Kojima, T. Tanaka, M. Iinuma, J. Nat. Prod. 1987, 50, 326;
- (1987) J. Nat. Prod. , vol.50 , pp. 326
- Mizuno, M.¹ Kojima, H.² Tanaka, T.³ Iinuma, M.⁴

25
- 0017818780
- b) M. Shamma, H. H. Tomlinson, J. Org. Chem. 1978, 43, 2852-2855.
- (1978) J. Org. Chem. , vol.43 , pp. 2852-2855
- Shamma, M.¹ Tomlinson, H.H.²

26
- 0002229630
- a) A. S. Bailey, C. R. Worthing, J. Chem. Soc. 1956, 4535-4543;
- (1956) J. Chem. Soc. , pp. 4535-4543
- Bailey, A.S.¹ Worthing, C.R.²

27
- 37049118491
- b) I. Ninomiya, T. Naito, H. Ishii, T. Ishida, M. Ueda, K. Harada, J. C. S. Perkin 11975, 762-764;
- (1975) J. C. S. Perkin 1 , pp. 762-764
- Ninomiya, I.¹ Naito, T.² Ishii, H.³ Ishida, T.⁴ Ueda, M.⁵ Harada, K.⁶

28
- 0026442519
- c) G. Martin, E. Guitian, L. Castedo, J. Org. Chem. 1992, 57, 5911-5917;
- (1992) J. Org. Chem. , vol.57 , pp. 5911-5917
- Martin, G.¹ Guitian, E.² Castedo, L.³

29
- 0000868224
- d) M. Cushman, J.-K. Chen, J. Org. Chem. 1987, 52, 1517-1521;
- (1987) J. Org. Chem. , vol.52 , pp. 1517-1521
- Cushman, M.¹ Chen, J.-K.²

30
- 0001451163
- e) M. Cushman, T.-C. Choong, J. T. Valko, M. P. Koleck, J. Org. Chem. 1980, 45, 5067-5073.
- (1980) J. Org. Chem. , vol.45 , pp. 5067-5073
- Cushman, M.¹ Choong, T.-C.² Valko, J.T.³ Koleck, M.P.⁴

31
- 0023880457
- a) R. D. Clark, Jahangir, J. Org. Chem. 1988, 53, 2378-2381;
- (1988) J. Org. Chem. , vol.53 , pp. 2378-2381
- Clark, R.D.¹ Jahangir²

32
- 1842689016
- b) T. N. Le, S. G. Gang, W. J. Cho, J. Org. Chem. 2004, 69, 2768-2772;
- (2004) J. Org. Chem. , vol.69 , pp. 2768-2772
- Le, T.N.¹ Gang, S.G.² Cho, W.J.³

33
- 1542358714
- c) T. N. Le, S. G. Gang, W. J. Cho, Tetrahedron Lett. 2004, 45, 2763-2766;
- (2004) Tetrahedron Lett. , vol.45 , pp. 2763-2766
- Le, T.N.¹ Gang, S.G.² Cho, W.J.³

34
- 0000129739
- d) G. S. Poindexter, J. Org. Chem. 1982, 47, 3787-3788.
- (1982) J. Org. Chem. , vol.47 , pp. 3787-3788
- Poindexter, G.S.¹

35
- 70350220535
- a) R. P. Korivi, W.-J. Wu, C.-H. Cheng, Chem. Eur. J. 2009, 15, 10727-10731;
- (2009) Chem. Eur. J. , vol.15 , pp. 10727-10731
- Korivi, R.P.¹ Wu, W.-J.² Cheng, C.-H.³

36
- 28244462079
- b) R. P. Korivi, C.-H. Cheng, Org. Lett. 2005, 7, 5179-5182;
- (2005) Org. Lett. , vol.7 , pp. 5179-5182
- Korivi, R.P.¹ Cheng, C.-H.²

37
- 16244420717
- 2]: c) E. A. Colby, K. C. O'Brie, T. F. Jamison, J. Am. Chem. Soc. 2005, 127, 4297;
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 4297
- Colby, E.A.¹ O'Brie, K.C.² Jamison, T.F.³

38
- 73949126664
- d) J. D. Trenkle, T. F. Jamison, Angew. Chem. 2009, 121, 5470-5472;
- (2009) Angew. Chem. , vol.121 , pp. 5470-5472
- Trenkle, J.D.¹ Jamison, T.F.²

39
- 70349900286
- Angew. Chem. Int. Ed. 2009, 48, 5366-5368;
- (2009) Angew. Chem. Int. Ed. , vol.48 , pp. 5366-5368

40
- 17144424570
- catalytic reaction by using imines: e) S. J. Patel, T. F. Jamison, Angew. Chem. 2004, 116, 4031-4034;
- (2004) Angew. Chem. , vol.116 , pp. 4031-4034
- Patel, S.J.¹ Jamison, T.F.²

41
- 4544296892
- Angew. Chem. Int. Ed. 2004, 43, 3941-3944;
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 3941-3944

42
- 55149113546
- f) C.-H. Yeh, R. P. Korivi, C.-H. Cheng, Angew. Chem. 2008, 120, 4970-4973;
- (2008) Angew. Chem. , vol.120 , pp. 4970-4973
- Yeh, C.-H.¹ Korivi, R.P.² Cheng, C.-H.³

43
- 53549109478
- Angew. Chem. Int. Ed. 2008, 47, 4892-4895;
- (2008) Angew. Chem. Int. Ed. , vol.47 , pp. 4892-4895

44
- 55149112396
- g) C.-C. Liu, R. P. Korivi, C.-H. Cheng, Chem. Eur. J. 2008, 14, 9503;
- (2008) Chem. Eur. J. , vol.14 , pp. 9503
- Liu, C.-C.¹ Korivi, R.P.² Cheng, C.-H.³

45
- 36849026774
- for isoquinoline derivatives: h) D. Fischer, H. Tomeba, N. K. Pahadi, N. T. Patil, Y. Yamamoto, Angew. Chem. 2007, 119, 4848-4850;
- (2007) Angew. Chem. , vol.119 , pp. 4848-4850
- Fischer, D.¹ Tomeba, H.² Pahadi, N.K.³ Patil, N.T.⁴ Yamamoto, Y.⁵

46
- 34347247306
- Angew. Chem. Int. Ed. 2007, 46, 4764-4766;
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 4764-4766

47
- 33746236851
- i) N. Asao, S. Yudha S., T. Nogami, Y. Yamamoto, Angew. Chem. 2005, 117, 5662-5664;
- (2005) Angew. Chem. , vol.117 , pp. 5662-5664
- Asao, N.¹ Yudha, S.S.² Nogami, T.³ Yamamoto, Y.⁴

48
- 24644476535
- Angew. Chem. Int. Ed. 2005, 44, 5526-5528;
- (2005) Angew. Chem. Int. Ed. , vol.44 , pp. 5526-5528

49
- 36849084104
- j) R. Yanada, S. Obika, H. Kono, Y. Takemoto, Angew. Chem. 2006, 118, 3906-3909;
- (2006) Angew. Chem. , vol.118 , pp. 3906-3909
- Yanada, R.¹ Obika, S.² Kono, H.³ Takemoto, Y.⁴

50
- 33746265841
- Angew. Chem. Int. Ed. 2006, 45, 3822-3825.
- (2006) Angew. Chem. Int. Ed. , vol.45 , pp. 3822-3825

51
- 37049069495
- a) M. Hanaoka, T. Motonishi, C. Mukai, J. C. S. Perkin I 1986, 2253-2256;
- (1986) J. C. S. Perkin i , pp. 2253-2256
- Hanaoka, M.¹ Motonishi, T.² Mukai, C.³

52
- 0037158232
- b) M. Treus, J. C. Estevez, L. Castedo, R. J. Estevez, Tetrahedron Lett. 2002, 43, 5323-5325;
- (2002) Tetrahedron Lett. , vol.43 , pp. 5323-5325
- Treus, M.¹ Estevez, J.C.² Castedo, L.³ Estevez, R.J.⁴

53
- 0021678079
- c) M. Hanaoka, H. Yamagishi, M. Marutani, C. Mukai, Tetrahedron Lett. 1984, 25, 5169-5172.
- (1984) Tetrahedron Lett. , vol.25 , pp. 5169-5172
- Hanaoka, M.¹ Yamagishi, H.² Marutani, M.³ Mukai, C.⁴

54
- 0032547125
- a) D. Gnecco, C. Marazano, R. G. Enriquez, J. L. Teran, M. R. Sanchez. S., A. Galindo, Tetrahedron: Asymmetry 1998, 9, 2027-2029;
- (1998) Tetrahedron: Asymmetry , vol.9 , pp. 2027-2029
- Gnecco, D.¹ Marazano, C.² Enriquez, R.G.³ Teran, J.L.⁴ Sanchez, M.R.S.⁵ Galindo, A.⁶

55
- 0038643951
- Wiley, New York
- b) S. D. Burke, R. L. Danheiser, Oxidizing and Reducing Agents Wiley, New York, 2000, p. 154.
- (2000) Oxidizing and Reducing Agents , pp. 154
- Burke, S.D.¹ Danheiser, R.L.²

56
- 33745699984
- a) J. C. Vardamides, Chem. Pharm. Bull. 2006, 54, 1034-1036;
- (2006) Chem. Pharm. Bull. , vol.54 , pp. 1034-1036
- Vardamides, J.C.¹

57
- 34247522312
- b) A. E. Mattson, K. A. Scheidt, J. Am. Chem. Soc. 2007, 129, 4508-4509;
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 4508-4509
- Mattson, A.E.¹ Scheidt, K.A.²

58
- 0343769330
- c) M. Hanaoka, W. J. Cho, S. Yoshida, T. Fueki, C. Mukai, Heterocycles 1989, 29, 857-860.
- (1989) Heterocycles , vol.29 , pp. 857-860
- Hanaoka, M.¹ Cho, W.J.² Yoshida, S.³ Fueki, T.⁴ Mukai, C.⁵

59
- 0025645809
- a) M. Hanaoka, W. J. Cho, S. Yoshida, T. Fueki, C. Mukai, Chem. Pharm. Bull. 1990, 38, 3335-3340.
- (1990) Chem. Pharm. Bull. , vol.38 , pp. 3335-3340
- Hanaoka, M.¹ Cho, W.J.² Yoshida, S.³ Fueki, T.⁴ Mukai, C.⁵

60
- 33745417849
- a) R. M. McFadden, B. M. Stoltz, J. Am. Chem. Soc. 2006, 128, 7738-7739;
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 7738-7739
- McFadden, R.M.¹ Stoltz, B.M.²

61
- 33947602410
- b) P. S. Baran, T. J. Maimone, J. M. Richter, Nature 2007, 446, 404-408;
- (2007) Nature , vol.446 , pp. 404-408
- Baran, P.S.¹ Maimone, T.J.² Richter, J.M.³

62
- 67650984682
- c) I. S. Young, P. S. Baran, Nat. Chem. 2009, 1, 193-205;
- (2009) Nat. Chem. , vol.1 , pp. 193-205
- Young, I.S.¹ Baran, P.S.²

63
- 68349116604
- d) K. Gademann, S. Bonnazi, Angew. Chem. 2007, 119, 5754-5756;
- (2007) Angew. Chem. , vol.119 , pp. 5754-5756
- Gademann, K.¹ Bonnazi, S.²

64
- 34547452720
- Angew. Chem. Int. Ed. 2007, 46, 5656-5658.
- (2007) Angew. Chem. Int. Ed. , vol.46 , pp. 5656-5658

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.