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Volumn 2014, Issue 13, 2014, Pages 2659-2663

A model study toward the concise synthesis of bromotyrosine-derived spiroisoxazoline natural products and analogous core structures

(3) Das, Prasanta a Valente, Edward J b Hamme, Ashton T a

a JACKSON STATE UNIVERSITY (United States)

b UNIVERSITY OF PORTLAND (United States)

Author keywords

Cyclization; Heterocycles; Multifunctionalization; Natural products; Spiro compounds; Synthetic methods

Indexed keywords

EID: 84899476843 PISSN: 1434193X EISSN: 10990690 Source Type: Journal
DOI: 10.1002/ejoc.201400009 Document Type: Article

Times cited : (10)

References (65)

1
- 0001885794
- Chemotaxonomy of the porifera: The development and current status of the field
- (Ed.:, P. J. Scheuer), Academic Press, New York
- P. R. Berquist, R. J. Wells, Chemotaxonomy of the Porifera: The Development and Current Status of the Field, in: Marine Natural Products: Chemical and Biological Perspectives (Ed.:, P. J. Scheuer), Academic Press, New York, 1983, vol. 5, p. 1-50.
- (1983) Marine Natural Products: Chemical and Biological Perspectives , vol.5 , pp. 1-50
- Berquist, P.R.¹ Wells, R.J.²

2
- 0032054664
- D. J. Faulkner, Nat. Prod. Rep. 1998, 15, 113.
- (1998) Nat. Prod. Rep. , vol.15 , pp. 113
- Faulkner, D.J.¹

3
- 0030841236
- previous reports in this series
- D. J. Faulkner, Nat. Prod. Rep. 1997, 14, 259, and previous reports in this series.
- (1997) Nat. Prod. Rep. , vol.14 , pp. 259
- Faulkner, D.J.¹

4
- 51849119622
- A.-A. M. Habib
- M. I. Abou-Shoer, L. A. Shaala, D. T. A. Youssef, J. M. Badr, A.-A. M. Habib, J. Nat. Prod. 2008, 71, 1464-1467.
- (2008) J. Nat. Prod. , vol.71 , pp. 1464-1467
- Abou-Shoer, M.I.¹ Shaala, L.A.² Youssef, D.T.A.³ Badr, J.M.⁴

5
- 0026762718
- S. P. Gunasekera, S. S. Cross, J. Nat. Prod. 1992, 55, 509-512.
- (1992) J. Nat. Prod. , vol.55 , pp. 509-512
- Gunasekera, S.P.¹ Cross, S.S.²

6
- 0025766030
- J. Kobayashi, M. Tsuda, K. Agemi, H. Shigemori, M. Ishibashi, T. Sasaki, Y. Mikami, Tetrahedron 1991, 47, 6617-6622.
- (1991) Tetrahedron , vol.47 , pp. 6617-6622
- Kobayashi, J.¹ Tsuda, M.² Agemi, K.³ Shigemori, H.⁴ Ishibashi, M.⁵ Sasaki, T.⁶ Mikami, Y.⁷

7
- 0034055182
- S. A. Ross, J. D. Weete, R. F. Schinazi, S. S. Wirtz, P. Tharnish, P. J. Scheuer, M. T. Hamann, J. Nat. Prod. 2000, 63, 501-503.
- (2000) J. Nat. Prod. , vol.63 , pp. 501-503
- Ross, S.A.¹ Weete, J.D.² Schinazi, R.F.³ Wirtz, S.S.⁴ Tharnish, P.⁵ Scheuer, P.J.⁶ Hamann, M.T.⁷

8
- 33846974766
- J.-H. Jang, R. W. M. van Soest, N. Fusetani, S. Matsunaga, J. Org. Chem. 2007, 72, 1211-1217.
- (2007) J. Org. Chem. , vol.72 , pp. 1211-1217
- Jang, J.-H.¹ Van Soest, R.W.M.² Fusetani, N.³ Matsunaga, S.⁴

9
- 0032405640
- I. Thironet, D. Daloze, J. C. Braekman, P. Willemsen, Nat. Prod. Lett. 1998, 12, 209-214.
- (1998) Nat. Prod. Lett. , vol.12 , pp. 209-214
- Thironet, I.¹ Daloze, D.² Braekman, J.C.³ Willemsen, P.⁴

10
- 0022376954
- H. Nakamura, H. Wu, J. Kobayashi, Tetrahedron Lett. 1985, 26, 4517-4520.
- (1985) Tetrahedron Lett. , vol.26 , pp. 4517-4520
- Nakamura, H.¹ Wu, H.² Kobayashi, J.³

11
- 62149098372
- M. W. B. McCulloch, G. S. Coombs, N. Banerjee, T. S. Bugni, K. M. Cannon, M. K. Harper, C. A. Veltri, D. M. Virshup, C. M. Ireland, Bioorg. Med. Chem. 2009, 17, 2189-2198.
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 2189-2198
- McCulloch, M.W.B.¹ Coombs, G.S.² Banerjee, N.³ Bugni, T.S.⁴ Cannon, K.M.⁵ Harper, M.K.⁶ Veltri, C.A.⁷ Virshup, D.M.⁸ Ireland, C.M.⁹

12
- 0028222730
- R. Mierzwa, A. King, M. A. Conover, S. Tozzi, M. S. Puar, M. Patel, S. J. Covan, J. Nat. Prod. 1994, 57, 175-177.
- (1994) J. Nat. Prod. , vol.57 , pp. 175-177
- Mierzwa, R.¹ King, A.² Conover, M.A.³ Tozzi, S.⁴ Puar, M.S.⁵ Patel, M.⁶ Covan, S.J.⁷

13
- 0035902239
- G. M. Nicholas, G. L. Newton, R. C. Fahey, C. A. Bewley, Org. Lett. 2001, 3, 1543-1545.
- (2001) Org. Lett. , vol.3 , pp. 1543-1545
- Nicholas, G.M.¹ Newton, G.L.² Fahey, R.C.³ Bewley, C.A.⁴

14
- 47549105779
- M. S. Buchanan, A. R. Carroll, G. A. Fechner, A. Boyle, M. Simpson, R. Addepalli, V. M. Avery, J. N. A. Hooper, T. Cheung, H. Chen, R. J. Quinn, J. Nat. Prod. 2008, 71, 1066-1067.
- (2008) J. Nat. Prod. , vol.71 , pp. 1066-1067
- Buchanan, M.S.¹ Carroll, A.R.² Fechner, G.A.³ Boyle, A.⁴ Simpson, M.⁵ Addepalli, R.⁶ Avery, V.M.⁷ Hooper, J.N.A.⁸ Cheung, T.⁹ Chen, H.¹⁰ Quinn, R.J.¹¹

15
- 68549088967
- T. Fujiwara, J.-H. Hwang, A. Kanamoto, H. Nagai, M. Takagi, S.-y. Kauzo, J. Antibiot. 2009, 62, 393-395.
- (2009) J. Antibiot. , vol.62 , pp. 393-395
- Fujiwara, T.¹ Hwang, J.-H.² Kanamoto, A.³ Nagai, H.⁴ Takagi, M.⁵ Kauzo, S.-Y.⁶

16
- 56249138249
- P. B. Shinde, Y. M. Lee, H. T. Dang, J. Hong, C.-O. Lee, J. H. Jung, Bioorg. Med. Chem. Lett. 2008, 18, 6414-6418.
- (2008) Bioorg. Med. Chem. Lett. , vol.18 , pp. 6414-6418
- Shinde, P.B.¹ Lee, Y.M.² Dang, H.T.³ Hong, J.⁴ Lee, C.-O.⁵ Jung, J.H.⁶

17
- 0028913755
- J. Kobayashi, K. Honma, T. Sasaki, M. Tsuda, Chem. Pharm. Bull. 1995, 43, 403-407.
- (1995) Chem. Pharm. Bull. , vol.43 , pp. 403-407
- Kobayashi, J.¹ Honma, K.² Sasaki, T.³ Tsuda, M.⁴

18
- 0000069626
- M. Murakata, K. Yamada, O. Hoshino, Heterocycles 1998, 47, 921-931.
- (1998) Heterocycles , vol.47 , pp. 921-931
- Murakata, M.¹ Yamada, K.² Hoshino, O.³

19
- 0028267993
- M. Murakata, K. Yamada, O. Hoshino, J. Chem. Soc., Chem. Commun. 1994, 443-444.
- (1994) J. Chem. Soc., Chem. Commun. , pp. 443-444
- Murakata, M.¹ Yamada, K.² Hoshino, O.³

20
- 37049085903
- M. Kacan, D. Koyuncu, A. McKillop, J. Chem. Soc. Perkin Trans. 1 1993, 1771-1776.
- (1993) J. Chem. Soc. Perkin Trans. 1 , pp. 1771-1776
- Kacan, M.¹ Koyuncu, D.² McKillop, A.³

21
- 0001011361
- H. Noda, M. Niwa, S. Yamamura, Tetrahedron Lett. 1981, 22, 3247-3248.
- (1981) Tetrahedron Lett. , vol.22 , pp. 3247-3248
- Noda, H.¹ Niwa, M.² Yamamura, S.³

22
- 37049118553
- A. R. Forrester, R. H. Thomson, S.-O. Woo, J. Chem. Soc. Perkin Trans. 1 1975, 2340-2348.
- (1975) J. Chem. Soc. Perkin Trans. 1 , pp. 2340-2348
- Forrester, A.R.¹ Thomson, R.H.² Woo, S.-O.³

23
- 37049140049
- A. R. Forrester, R. H. Thomson, S.-O. Woo, J. Chem. Soc. Perkin Trans. 1 1975, 2348-2353.
- (1975) J. Chem. Soc. Perkin Trans. 1 , pp. 2348-2353
- Forrester, A.R.¹ Thomson, R.H.² Woo, S.-O.³

24
- 0000746811
- K. T. Okamoto, J. Clardy, Tetrahedron Lett. 1987, 28, 4969-4972.
- (1987) Tetrahedron Lett. , vol.28 , pp. 4969-4972
- Okamoto, K.T.¹ Clardy, J.²

25
- 1542793010
- A. R. Forrester, R. H. Thomson, S.-O. Woo, Justus Liebigs Ann. Chem. 1978, 66-73.
- (1978) Justus Liebigs Ann. Chem. , pp. 66-73
- Forrester, A.R.¹ Thomson, R.H.² Woo, S.-O.³

26
- 0001322922
- M. Murakata, T. Masafumi, O. Hoshino, J. Org. Chem. 1997, 62, 4428-4433.
- (1997) J. Org. Chem. , vol.62 , pp. 4428-4433
- Murakata, M.¹ Masafumi, T.² Hoshino, O.³

27
- 0000943756
- S. Nishiyama, S. Yamamura, Tetrahedron Lett. 1983, 24, 3351-3352.
- (1983) Tetrahedron Lett. , vol.24 , pp. 3351-3352
- Nishiyama, S.¹ Yamamura, S.²

28
- 0022298152
- S. Nishiyama, S. Yamamura, Bull. Chem. Soc. Jpn. 1985, 58, 3453-3456.
- (1985) Bull. Chem. Soc. Jpn. , vol.58 , pp. 3453-3456
- Nishiyama, S.¹ Yamamura, S.²

29
- 0142246553
- T. Ogamino, S. Nishiyama, Tetrahedron 2003, 59, 9419-9423.
- (2003) Tetrahedron , vol.59 , pp. 9419-9423
- Ogamino, T.¹ Nishiyama, S.²

30
- 0345761293
- T. Ogamino, Y. Ishikawa, S. Nishiyama, Heterocycles 2003, 61, 73-78.
- (2003) Heterocycles , vol.61 , pp. 73-78
- Ogamino, T.¹ Ishikawa, Y.² Nishiyama, S.³

31
- 78650080824
- J. W. Shearman, R. M. Myers, J. D. Brentonb, S. V. Ley, Org. Biomol. Chem. 2011, 9, 62-65.
- (2011) Org. Biomol. Chem. , vol.9 , pp. 62-65
- Shearman, J.W.¹ Myers, R.M.² Brentonb, J.D.³ Ley, S.V.⁴

32
- 0035804954
- T. R. Boehlow, J. J. Harburn, C. D. Spilling, J. Org. Chem. 2001, 66, 3111-3118.
- (2001) J. Org. Chem. , vol.66 , pp. 3111-3118
- Boehlow, T.R.¹ Harburn, J.J.² Spilling, C.D.³

33
- 0003115609
- H. Togo, G. Nogami, M. Yokoyama, Synlett 1998, 534-536.
- (1998) Synlett , pp. 534-536
- Togo, H.¹ Nogami, G.² Yokoyama, M.³

34
- 0001645943
- S. V. Ley, A. W. Thomas, H. Finch, J. Chem. Soc. Perkin Trans. 1 1999, 669-671.
- (1999) J. Chem. Soc. Perkin Trans. 1 , pp. 669-671
- Ley, S.V.¹ Thomas, A.W.² Finch, H.³

35
- 23044495915
- J. J. Harburn, N. P. Rath, C. D. Spilling, J. Org. Chem. 2005, 70, 6398-6403.
- (2005) J. Org. Chem. , vol.70 , pp. 6398-6403
- Harburn, J.J.¹ Rath, N.P.² Spilling, C.D.³

36
- 0030592824
- M. Murakata, K. Yamada, O. Hoshino, Tetrahedron 1996, 52, 14713-14722.
- (1996) Tetrahedron , vol.52 , pp. 14713-14722
- Murakata, M.¹ Yamada, K.² Hoshino, O.³

37
- 0031904058
- H. H. Wasserman, J. Wang, J. Org. Chem. 1998, 63, 5581-5586.
- (1998) J. Org. Chem. , vol.63 , pp. 5581-5586
- Wasserman, H.H.¹ Wang, J.²

38
- 73949137170
- F. Hentschel, T. Lindel, Synthesis 2010, 0181-0204.
- (2010) Synthesis , pp. 0181-0204
- Hentschel, F.¹ Lindel, T.²

39
- 33845284816
- J. Xu, J. Wang, E. D. Ellis, A. T. Hamme II, Synthesis 2006, 3815-3818.
- (2006) Synthesis , pp. 3815-3818
- Xu, J.¹ Wang, J.² Ellis, E.D.³ Hamme II, A.T.⁴

40
- 68349148072
- E. D. Ellis, J. Xu, E. J. Valente, A. T. Hamme II, Tetrahedron Lett. 2009, 50, 5516-5519.
- (2009) Tetrahedron Lett. , vol.50 , pp. 5516-5519
- Ellis, E.D.¹ Xu, J.² Valente, E.J.³ Hamme II, A.T.⁴

41
- 0025175992
- D. P. Shrout, D. A. Lightner, Synthesis 1990, 1062-1065.
- (1990) Synthesis , pp. 1062-1065
- Shrout, D.P.¹ Lightner, D.A.²

42
- 77957107796
- Z. Gu, A. Zakarian, Org. Lett. 2010, 12, 4224-4227.
- (2010) Org. Lett. , vol.12 , pp. 4224-4227
- Gu, Z.¹ Zakarian, A.²

43
- 0028147411
- K. Takahashi, T. Tanaka, T. Suzuki, M. Hirama, Tetrahedron 1994, 50, 1327-1340.
- (1994) Tetrahedron , vol.50 , pp. 1327-1340
- Takahashi, K.¹ Tanaka, T.² Suzuki, T.³ Hirama, M.⁴

44
- 0026089158
- B.-C. Chen, M. C. Weismiller, F. A. Davis, D. Boschelli, J. R. Empfield, A. B. Smith III, Tetrahedron 1991, 47, 173-182.
- (1991) Tetrahedron , vol.47 , pp. 173-182
- Chen, B.-C.¹ Weismiller, M.C.² Davis, F.A.³ Boschelli, D.⁴ Empfield, J.R.⁵ Smith III, A.B.⁶

45
- 0038597485
- A. S. Demir, O. Sesenoglu, Org. Lett. 2002, 4, 2021-2023.
- (2002) Org. Lett. , vol.4 , pp. 2021-2023
- Demir, A.S.¹ Sesenoglu, O.²

46
- 0026685708
- P. H. Nelson, J. T. Nelson, Synthesis 1992, 1287-1291.
- (1992) Synthesis , pp. 1287-1291
- Nelson, P.H.¹ Nelson, J.T.²

47
- 0001585505
- M. J. Mphahlele, T. A. Modro, J. Org. Chem. 1995, 60, 8236-8240.
- (1995) J. Org. Chem. , vol.60 , pp. 8236-8240
- Mphahlele, M.J.¹ Modro, T.A.²

48
- 0032736221
- W. Adam, M. Lazarus, C. R. Saha-Möller, P. Schreier, Acc. Chem. Res. 1999, 32, 837-845.
- (1999) Acc. Chem. Res. , vol.32 , pp. 837-845
- Adam, W.¹ Lazarus, M.² Saha-Möller, C.R.³ Schreier, P.⁴

49
- 33745762337
- R. N. Patel, Curr. Org. Chem. 2006, 10, 1289-1321.
- (2006) Curr. Org. Chem. , vol.10 , pp. 1289-1321
- Patel, R.N.¹

50
- 33645031872
- L. C. Henderson, W. A. Loughlin, I. D. Jenkins, P. C. Healy, M. R. Campitelli, J. Org. Chem. 2006, 71, 2384-2388.
- (2006) J. Org. Chem. , vol.71 , pp. 2384-2388
- Henderson, L.C.¹ Loughlin, W.A.² Jenkins, I.D.³ Healy, P.C.⁴ Campitelli, M.R.⁵

51
- 82255175658
- G. Majetich, Y. Zhang, X. Tian, J. E. Britton, Y. Li, R. Phillips, Tetrahedron 2011, 67, 10129-10146.
- (2011) Tetrahedron , vol.67 , pp. 10129-10146
- Majetich, G.¹ Zhang, Y.² Tian, X.³ Britton, J.E.⁴ Li, Y.⁵ Phillips, R.⁶

52
- 77953127349
- K. Wińska, A. Grudniewska, A. Chojnacka, A. Białoń ska, C. Wawrzeńczyk, Tetrahedron: Asymmetry 2010, 21, 670-678.
- (2010) Tetrahedron: Asymmetry , vol.21 , pp. 670-678
- Wińska, K.¹ Grudniewska, A.² Chojnacka, A.³ Białońska, A.⁴ Wawrzeńczyk, C.⁵

53
- 33745762337
- R. N. Patel, Curr. Org. Chem. 2006, 10, 1289-1321.
- (2006) Curr. Org. Chem. , vol.10 , pp. 1289-1321
- Patel, R.N.¹

54
- 0035064070
- A. Clerici, N. Pastori, O. Porta, Tetrahedron 2001, 57, 217-225.
- (2001) Tetrahedron , vol.57 , pp. 217-225
- Clerici, A.¹ Pastori, N.² Porta, O.³

55
- 20944434191
- K. C. Nicolaou, T. Montagnon, G. Vassilikogiannakis, C. J. N. Mathison, J. Am. Chem. Soc. 2005, 127, 8872-8888.
- (2005) J. Am. Chem. Soc. , vol.127 , pp. 8872-8888
- Nicolaou, K.C.¹ Montagnon, T.² Vassilikogiannakis, G.³ Mathison, C.J.N.⁴

56
- 0033945102
- R. D. Encarnaciõn, E. Sandoval, J. Mamstrøm, C. Christophersen, J. Nat. Prod. 2000, 63, 874-875.
- (2000) J. Nat. Prod. , vol.63 , pp. 874-875
- Encarnaciõn, R.D.¹ Sandoval, E.² Mamstrøm, J.³ Christophersen, C.⁴

57
- 0000776502
- G. M. Konig, A. D. Wright, Heterocycles 1993, 36, 1351-1359.
- (1993) Heterocycles , vol.36 , pp. 1351-1359
- Konig, G.M.¹ Wright, A.D.²

58
- 0035523860
- A. Kijjoa, R. Watanadilok, P. Sonchaeng, A. M. S. Silva, G. Eaton, W. Herz, Z. Naturforsch. C 2001, 56, 1116-1119.
- (2001) Z. Naturforsch. C , vol.56 , pp. 1116-1119
- Kijjoa, A.¹ Watanadilok, R.² Sonchaeng, P.³ Silva, A.M.S.⁴ Eaton, G.⁵ Herz, W.⁶

59
- 33644959976
- S. Bardhan, D. C. Schmitt, J. A. Porco Jr., Org. Lett. 2006, 8, 927-930.
- (2006) Org. Lett. , vol.8 , pp. 927-930
- Bardhan, S.¹ Schmitt, D.C.² Porco Jr., J.A.³

60
- 0037009040
- K. C. Nicolaou, G. Vassilikogiannakis, T. Montagnon, Angew. Chem. Int. Ed. 2002, 41, 3276-3281
- (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 3276-3281
- Nicolaou, K.C.¹ Vassilikogiannakis, G.² Montagnon, T.³

61
- 0038271079
- Angew. Chem. 2002, 114, 3410-3415.
- (2002) Angew. Chem. , vol.114 , pp. 3410-3415

62
- 0036979945
- K. C. Nicolaou, T. Montagnon, G. Vassilikogiannakis, Chem. Commun. 2002, 2478-2479.
- (2002) Chem. Commun. , pp. 2478-2479
- Nicolaou, K.C.¹ Montagnon, T.² Vassilikogiannakis, G.³

63
- 84899472147
- CCDC-967652 (for 10) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via
- CCDC-967652 (for 10) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/datarequest/cif.

64
- 33747849809
- Prepared by using a literature procedure
- Prepared by using a literature procedure:, W. J. Gensler, F. A. Johnson, D. B. Sloan, J. Am. Chem. Soc. 1960, 82, 6074-6081.
- (1960) J. Am. Chem. Soc. , vol.82 , pp. 6074-6081
- Gensler, W.J.¹ Johnson, F.A.² Sloan, D.B.³

65
- 0000814428
- T. Nakata, T. Tanaka, T. Oishi, Tetrahedron Lett. 1981, 22, 4723-4726.
- (1981) Tetrahedron Lett. , vol.22 , pp. 4723-4726
- Nakata, T.¹ Tanaka, T.² Oishi, T.³

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