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Volumn , Issue 45, 2007, Pages 4764-4766

Palladium-catalysed N-annulation routes to indoles: The synthesis of indoles with sterically demanding N-substituents, including demethylasterriquinone A1

(3) Fletcher, Anthony J a Bax, Matthew N b Willis, Michael C a

a UNIVERSITY OF OXFORD (United Kingdom)

b University of Bath Claverton Down (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

DEMETHYLASTERRIQUINONE A1; INDOLE DERIVATIVE; PALLADIUM; UNCLASSIFIED DRUG;

ANNULATION REACTION; ARTICLE; CHEMICAL BOND; STEREOSPECIFICITY; SYNTHESIS;

EID: 36148978880 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b712227f Document Type: Article

Times cited : (63)

References (41)

1
- 0003979828
- Academic Press, London
- R. J. Sundberg, Indoles, Academic Press, London, 1996
- (1996) Indoles
- Sundberg, R.J.¹

2
- 0034615797
- Selected examples: N-alkyl indoles:
- G. W. Gribble J. Chem. Soc., Perkin Trans. 1 2000 1045
- (2000) J. Chem. Soc., Perkin Trans. 1 , pp. 1045
- Gribble, G.W.¹

3
- 13344275848
- L. F. Kuyper D. P. Baccanari M. L. Jones R. N. Hunter R. L. Tansik S. S. Joyner C. M. Boytos S. K. Rudolph V. Knick H. R. Wilson J. M. Caddell H. S. Friedman J. C. W. Comley J. N. Stables J. Med. Chem. 1996 39 892
- (1996) J. Med. Chem. , vol.39 , pp. 892
- Kuyper, L.F.¹ Baccanari, D.P.² Jones, M.L.³ Hunter, R.N.⁴ Tansik, R.L.⁵ Joyner, S.S.⁶ Boytos, C.M.⁷ Rudolph, S.K.⁸ Knick, V.⁹ Wilson, H.R.¹⁰ Caddell, J.M.¹¹ Friedman, H.S.¹² Comley, J.C.W.¹³ Stables, J.N.¹⁴

4
- 0037248374
- J. W. Huffman R. Mabon M.-J. Wu J. Lu R. Hart D. P. Hurst P. H. Reggio J. L. Wiley B. R. Martin Bioorg. Med. Chem. 2003 11 539
- (2003) Bioorg. Med. Chem. , vol.11 , pp. 539
- Huffman, J.W.¹ Mabon, R.² Wu, M.-J.³ Lu, J.⁴ Hart, R.⁵ Hurst, D.P.⁶ Reggio, P.H.⁷ Wiley, J.L.⁸ Martin, B.R.⁹

5
- 33646748549
- N-arylated indoles:
- B. P. Smart R. C. Oslund L. A. Walsh M. H. Gelb J. Med. Chem. 2006 49 2858
- (2006) J. Med. Chem. , vol.49 , pp. 2858
- Smart, B.P.¹ Oslund, R.C.² Walsh, L.A.³ Gelb, M.H.⁴

6
- 14444284336
- G. Spadoni C. Balsamini A. Bedini G. Diamantini B. Di Giacomo A. Tontini G. Tarzia M. Mor P. V. Plazzi S. Rivara R. Nonno M. Pannacci V. Lucini F. Frachini B. M. Stankov J. Med. Chem. 1998 41 3624
- (1998) J. Med. Chem. , vol.41 , pp. 3624
- Spadoni, G.¹ Balsamini, C.² Bedini, A.³ Diamantini, G.⁴ Di Giacomo, B.⁵ Tontini, A.⁶ Tarzia, G.⁷ Mor, M.⁸ Plazzi, P.V.⁹ Rivara, S.¹⁰ Nonno, R.¹¹ Pannacci, M.¹² Lucini, V.¹³ Frachini, F.¹⁴ Stankov, B.M.¹⁵

7
- 0029661891
- K. Andersen T. Liljefors J. Hyttel J. Perregaard J. Med. Chem. 1996 39 3723
- (1996) J. Med. Chem. , vol.39 , pp. 3723
- Andersen, K.¹ Liljefors, T.² Hyttel, J.³ Perregaard, J.⁴

8
- 0019178012
- C. A. Harbert J. J. Plattner W. M. Welch J. Med. Chem. 1980 23 635
- (1980) J. Med. Chem. , vol.23 , pp. 635
- Harbert, C.A.¹ Plattner, J.J.² Welch, W.M.³

9
- 36148948290
- E. J. Thomas, Thieme, Stuttgart, p. 361
- J. A. Joule, in Science of Synthesis, ed., E. J. Thomas,, Thieme, Stuttgart, 2000, vol. 10, ch. 13, p. 361
- (2000) Science of Synthesis, Ed.
- Joule In, J.A.¹

10
- 0034739182
- L. M. Levy G. M. Cabrera J. E. Wright A. M. Seldes Phytochemistry 2000 54 941
- (2000) Phytochemistry , vol.54 , pp. 941
- Levy, L.M.¹ Cabrera, G.M.² Wright, J.E.³ Seldes, A.M.⁴

11
- 0017110558
- Y. Yamamoto K. Nishiyama N. Kiriyama Chem. Pharm. Bull. 1976 24 1853
- (1976) Chem. Pharm. Bull. , vol.24 , pp. 1853
- Yamamoto, Y.¹ Nishiyama, K.² Kiriyama, N.³

12
- 0037010810
- G. D. Sala D. Capozzo I. Izzo A. Giordano A. Iommazzo A. Spinella Tetrahedron Lett. 2002 43 8839
- (2002) Tetrahedron Lett. , vol.43 , pp. 8839
- Sala, G.D.¹ Capozzo, D.² Izzo, I.³ Giordano, A.⁴ Iommazzo, A.⁵ Spinella, A.⁶

13
- 3042750493
- F. Yokokawa H. Sugiyama T. Aoyama T. Shioiri Synthesis 2004 1476
- (2004) Synthesis , pp. 1476
- Yokokawa, F.¹ Sugiyama, H.² Aoyama, T.³ Shioiri, T.⁴

14
- 0038296199
- P. S. Baran C. A. Guerrero E. J. Corey J. Am. Chem. Soc. 2003 125 5628
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 5628
- Baran, P.S.¹ Guerrero, C.A.² Corey, E.J.³

15
- 0141631742
- J. M. Roe R. A. B. Webster A. Ganasan Org. Lett. 2003 5 2825
- (2003) Org. Lett. , vol.5 , pp. 2825
- Roe, J.M.¹ Webster, R.A.B.² Ganasan, A.³

16
- 30944431682
- D. B. Hansen A. S. Lewis S. J. Gavalas M. M. Joullié Tetrahedron: Asymmetry 2006 17 15
- (2006) Tetrahedron: Asymmetry , vol.17 , pp. 15
- Hansen, D.B.¹ Lewis, A.S.² Gavalas, S.J.³ Joullié, M.M.⁴

17
- 12344275854
- M. C. Willis G. N. Brace I. P. Holmes Angew. Chem., Int. Ed. 2005 44 403
- (2005) Angew. Chem., Int. Ed. , vol.44 , pp. 403
- Willis, M.C.¹ Brace, G.N.² Holmes, I.P.³

18
- 33744799129
- For reviews of Pd-catalysed C-N and C-O cross-coupling of aryl halides, see:
- M. C. Willis G. N. Brace T. J. K. Findlay I. P. Holmes Adv. Synth. Catal. 2006 348 851
- (2006) Adv. Synth. Catal. , vol.348 , pp. 851
- Willis, M.C.¹ Brace, G.N.² Findlay, T.J.K.³ Holmes, I.P.⁴

19
- 0003995267
- E. I. Negishi, Wiley-Interscience, New York, p. 1051
- J. F. Hartwig, in Handbook of Organopalladium Chemistry for Organic Synthesis, ed., E. I. Negishi,, Wiley-Interscience, New York, 2002, vol. 1, p. 1051
- (2002) Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.
- Hartwig In, J.F.¹

20
- 0003995267
- E. I. Negishi, Wiley-Interscience, New York, p. 1097
- J. F. Hartwig, in Handbook of Organopalladium Chemistry for Organic Synthesis, ed., E. I. Negishi,, Wiley-Interscience, New York, 2002, vol. 1, p. 1097
- (2002) Handbook of Organopalladium Chemistry for Organic Synthesis, Ed.
- Hartwig In, J.F.¹

21
- 0000157513
- A. R. Muci S. L. Buchwald Top. Curr. Chem. 2002 219 131
- (2002) Top. Curr. Chem. , vol.219 , pp. 131
- Muci, A.R.¹ Buchwald, S.L.²

22
- 0037060980
- Amine 3 was prepared in multigram quantities by thermal [3,3]-rearrangement of the corresponding trichloroacetimidate derivative, followed by NaOH mediated hydrolysis. Based on the procedure of Itoh et al.:
- D. Prim J.-M. Campagne D. Joseph B. Andrioletti Tetrahedron 2002 58 2041
- (2002) Tetrahedron , vol.58 , pp. 2041
- Prim, D.¹ Campagne, J.-M.² Joseph, D.³ Andrioletti, B.⁴

23
- 0001386690
- H. Nagashima H. Wakamatsu N. Ozaki T. Ishii M. Watanabe T. Tajima K. Itoh J. Org. Chem. 1992 57 1682
- (1992) J. Org. Chem. , vol.57 , pp. 1682
- Nagashima, H.¹ Wakamatsu, H.² Ozaki, N.³ Ishii, T.⁴ Watanabe, M.⁵ Tajima, T.⁶ Itoh, K.⁷

24
- 3042654141
- S. D. Walker T. E. Barder J. R. Martinelli S. L. Buchwald Angew. Chem., Int. Ed. 2004 43 1871
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 1871
- Walker, S.D.¹ Barder, T.E.² Martinelli, J.R.³ Buchwald, S.L.⁴

25
- 0038579438
- X. Huang K. W. Anderson D. Zim L. Jiang A. Klapars S. L. Buchwald J. Am. Chem. Soc. 2003 125 6653
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 6653
- Huang, X.¹ Anderson, K.W.² Zim, D.³ Jiang, L.⁴ Klapars, A.⁵ Buchwald, S.L.⁶

26
- 0034600318
- A. F. Littke C. Dai G. C. Fu J. Am. Chem. Soc. 2000 122 4020
- (2000) J. Am. Chem. Soc. , vol.122 , pp. 4020
- Littke, A.F.¹ Dai, C.² Fu, G.C.³

27
- 0035961019
- For an earlier synthesis of demethylasterriquinone A1, see:
- M. R. Netherton G. C. Fu Org. Lett. 2001 3 4295
- (2001) Org. Lett. , vol.3 , pp. 4295
- Netherton, M.R.¹ Fu, G.C.²

28
- 0037111792
- M. C. Pirrung Z. Li K. Park J. Zhu J. Org. Chem. 2002 67 7919
- (2002) J. Org. Chem. , vol.67 , pp. 7919
- Pirrung, M.C.¹ Li, Z.² Park, K.³ Zhu, J.⁴

29
- 0025666439
- K. Arai Y. Yamamoto Chem. Pharm. Bull. 1990 38 2929
- (1990) Chem. Pharm. Bull. , vol.38 , pp. 2929
- Arai, K.¹ Yamamoto, Y.²

30
- 0030775174
- A. Kaji R. Saito M. Nomura K. Miyamoto N. Kiriyama Anticancer Res. 1997 17 3675
- (1997) Anticancer Res. , vol.17 , pp. 3675
- Kaji, A.¹ Saito, R.² Nomura, M.³ Miyamoto, K.⁴ Kiriyama, N.⁵

31
- 0033532347
- B. Zhang G. Salituro D. Szalkowski Z. Li Y. Zhang I. Royo D. Vilella M. T. Díez F. Pelaez C. Ruby R. L. Kendall X. Mao P. Griffin J. Calaycay J. R. Zierath J. V. Heck R. G. Smith D. E. Moller Science 1999 284 974
- (1999) Science , vol.284 , pp. 974
- Zhang, B.¹ Salituro, G.² Szalkowski, D.³ Li, Z.⁴ Zhang, Y.⁵ Royo, I.⁶ Vilella, D.⁷ Díez, M.T.⁸ Pelaez, F.⁹ Ruby, C.¹⁰ Kendall, R.L.¹¹ Mao, X.¹² Griffin, P.¹³ Calaycay, J.¹⁴ Zierath, J.R.¹⁵ Heck, J.V.¹⁶ Smith, R.G.¹⁷ Moller, D.E.¹⁸

32
- 0000546703
- G. D. Harris, Jr. A. Nguyen H. App P. Hirth G. McMahon C. Tang Org. Lett. 1999 1 431
- (1999) Org. Lett. , vol.1 , pp. 431
- Harris Jr., G.D.¹ Nguyen, A.² App, H.³ Hirth, P.⁴ McMahon, G.⁵ Tang, C.⁶

33
- 0345276525
- J. S. Yadav B. V. S. Reddy T. Swamy Tetrahedron Lett. 2003 44 9121
- (2003) Tetrahedron Lett. , vol.44 , pp. 9121
- Yadav, J.S.¹ Reddy, B.V.S.² Swamy, T.³

34
- 0347949534
- J. S. Yadav B. V. S. Reddy T. Swamy Synthesis 2004 106
- (2004) Synthesis , pp. 106
- Yadav, J.S.¹ Reddy, B.V.S.² Swamy, T.³

35
- 33144475097
- H.-B. Zhang L. Liu Y.-J. Chen D. Wang C.-J. Li Eur. J. Org. Chem. 2006 869
- (2006) Eur. J. Org. Chem. , pp. 869
- Zhang, H.-B.¹ Liu, L.² Chen, Y.-J.³ Wang, D.⁴ Li, C.-J.⁵

36
- 26844563741
- Also see ref. 12
- S. Koulouri E. Malamidou-Xenikaki S. Spyroudis Tetrahedron 2005 61 10894
- (2005) Tetrahedron , vol.61 , pp. 10894
- Koulouri, S.¹ Malamidou-Xenikaki, E.² Spyroudis, S.³

37
- 0035825781
- M. C. Pirrung K. Park Z. Li Org. Lett. 2001 3 365
- (2001) Org. Lett. , vol.3 , pp. 365
- Pirrung, M.C.¹ Park, K.² Li, Z.³

38
- 0037195656
- M. C. Pirrung L. Deng Z. Li K. Park J. Org. Chem. 2002 67 8374
- (2002) J. Org. Chem. , vol.67 , pp. 8374
- Pirrung, M.C.¹ Deng, L.² Li, Z.³ Park, K.⁴

39
- 16844378606
- M. C. Pirrung Y. Liu L. Deng D. K. Halstead Z. Li J. F. May M. Wedel D. A. Austin N. J. G. Webster J. Am. Chem. Soc. 2005 127 4609
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 4609
- Pirrung, M.C.¹ Liu, Y.² Deng, L.³ Halstead, D.K.⁴ Li, Z.⁵ May, J.F.⁶ Wedel, M.⁷ Austin, D.A.⁸ Webster, N.J.G.⁹

40
- 34948824936
- 10.1021/cc070062m
- M. C. Pirrung Z. Li E. Hensley Y. Liu A. Tanksale B. Lin A. Pai N. J. G. Webster J. Comb. Chem. 2007 10.1021/cc070062m
- (2007) J. Comb. Chem.
- Pirrung, M.C.¹ Li, Z.² Hensley, E.³ Liu, Y.⁴ Tanksale, A.⁵ Lin, B.⁶ Pai, A.⁷ Webster, N.J.G.⁸

41
- 17044417287
- M. C. Pirrung K. Fujita K. Park J. Org. Chem. 2005 70 2537
- (2005) J. Org. Chem. , vol.70 , pp. 2537
- Pirrung, M.C.¹ Fujita, K.² Park, K.³

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