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Volumn , Issue 29, 2008, Pages 3432-3434

A two-directional approach to the anatoxin alkaloids: Second synthesis of homoanatoxin and efficient synthesis of anatoxin-a

(2) Roe, Stephen J a Stockman, Robert A a,b

a UNIVERSITY OF EAST ANGLIA (United Kingdom)

b UNIVERSITY OF NOTTINGHAM (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; ANATOXIN; ANATOXIN A; HOMOANATOXIN;

ARTICLE; CHEMICAL REACTION KINETICS; CYCLIZATION; DEPROTECTION REACTION; HORNER WADSWORTH EMMONS REACTION; MANNICH REACTION; MICHAEL ADDITION; MITSUNOBU REACTION; OXIDATION; TOXIN SYNTHESIS;

EID: 47549118512 PISSN: 13597345 EISSN: None Source Type: Journal
DOI: 10.1039/b804304c Document Type: Article

Times cited : (26)

References (23)

1
- 0016438986
- W. W. Carmichael D. F. Biggs P. R. Gorham Science 1975 187 542
- (1975) Science , vol.187 , pp. 542
- Carmichael, W.W.¹ Biggs, D.F.² Gorham, P.R.³

2
- 0000984836
- J. P. Delvin O. E. Edwards P. R. Gorham N. R. Hunter R. K. Pike B. Stavric Can. J. Chem. 1977 55 1367
- (1977) Can. J. Chem. , vol.55 , pp. 1367
- Delvin, J.P.¹ Edwards, O.E.² Gorham, P.R.³ Hunter, N.R.⁴ Pike, R.K.⁵ Stavric, B.⁶

3
- 19344373344
- M. Gugger S. Lenoir C. Berger A. Ledreux J. C. Druart J. F. Humbert C. Guette C. Bernard Toxicon 2005 45 919
- (2005) Toxicon , vol.45 , pp. 919
- Gugger, M.¹ Lenoir, S.² Berger, C.³ Ledreux, A.⁴ Druart, J.C.⁵ Humbert, J.F.⁶ Guette, C.⁷ Bernard, C.⁸

4
- 0026808336
- C. Edwards K. A. Beattie C. M. Scrimgeour G. A. Codd Toxicon 1992 30 1165
- (1992) Toxicon , vol.30 , pp. 1165
- Edwards, C.¹ Beattie, K.A.² Scrimgeour, C.M.³ Codd, G.A.⁴

5
- 0024403199
- K. Sivonen K. Himberg R. Luukkainen S. I. Niemelae G. K. Poon G. A. Codd Toxic. Assess. 1989 4 339
- (1989) Toxic. Assess. , vol.4 , pp. 339
- Sivonen, K.¹ Himberg, K.² Luukkainen, R.³ Niemelae, S.I.⁴ Poon, G.K.⁵ Codd, G.A.⁶

6
- 33846354888
- S. A. Wood D. J. Stirling L. R. Briggs J. Sprosen P. Holland J. G. Ruck R. G. N. Z. Wear J. Mar. Freshwater Res. 2006 40 585
- (2006) J. Mar. Freshwater Res. , vol.40 , pp. 585
- Wood, S.A.¹ Stirling, D.J.² Briggs, L.R.³ Sprosen, J.⁴ Holland, P.⁵ Ruck, J.G.⁶ Wear, R.G.N.Z.⁷

7
- 3042517872
- E. Viaggiu S. Melchiorre F. Volpi A. Di Corcia R. Mancini L. Garibaldi G. Crichigno M. Bruno Environ. Toxicol. 2004 19 191
- (2004) Environ. Toxicol. , vol.19 , pp. 191
- Viaggiu, E.¹ Melchiorre, S.² Volpi, F.³ Di Corcia, A.⁴ Mancini, R.⁵ Garibaldi, L.⁶ Crichigno, G.⁷ Bruno, M.⁸

8
- 1542496610
- M. Namikoshi T. Murakami M. F. Watanabe T. Oda J. Yamada S. Tsujimura H. Nagai S. Oishi Toxicon 2003 42 533
- (2003) Toxicon , vol.42 , pp. 533
- Namikoshi, M.¹ Murakami, T.² Watanabe, M.F.³ Oda, T.⁴ Yamada, J.⁵ Tsujimura, S.⁶ Nagai, H.⁷ Oishi, S.⁸

9
- 10044258826
- A. Ballot L. Krienitz K. Kotut C. Wiegand S. Pflugmacher Harmful Algae 2005 4 139
- (2005) Harmful Algae , vol.4 , pp. 139
- Ballot, A.¹ Krienitz, L.² Kotut, K.³ Wiegand, C.⁴ Pflugmacher, S.⁵

10
- 0026526924
- S. Wonnacott K. L. Swanson E. X. Albuquerque N. J. S. Huby P. Thompson T. Gallagher Biochem. Pharmacol. 1992 43 419
- (1992) Biochem. Pharmacol. , vol.43 , pp. 419
- Wonnacott, S.¹ Swanson, K.L.² Albuquerque, E.X.³ Huby, N.J.S.⁴ Thompson, P.⁵ Gallagher, T.⁶

11
- 0026577946
- For a recent review on the pharmacology of anatoxin-a and analogues, see:
- O. M. Skulberg W. W. Carmichael R. A. Andersen S. Matsunaga R. E. Moore R. Skulberg Environ. Toxicol. Chem. 1992 11 321
- (1992) Environ. Toxicol. Chem. , vol.11 , pp. 321
- Skulberg, O.M.¹ Carmichael, W.W.² Andersen, R.A.³ Matsunaga, S.⁴ Moore, R.E.⁵ Skulberg, R.⁶

12
- 33646786810
- S. Wonnacott T. Gallagher Mar. Drugs 2006 4 228
- (2006) Mar. Drugs , vol.4 , pp. 228
- Wonnacott, S.¹ Gallagher, T.²

13
- 29144435115
- For reviews on synthetic approaches to anatoxin-a, see:
- C. B. Cassels I. Bermudez F. Dajas J. A. Abin-Carriquiry S. Wonnacott Drug Discovery Today 2005 10 1657
- (2005) Drug Discovery Today , vol.10 , pp. 1657
- Cassels, C.B.¹ Bermudez, I.² Dajas, F.³ Abin-Carriquiry, J.A.⁴ Wonnacott, S.⁵

14
- 0029914328
- H. L. Mansell Tetrahedron 1996 52 6025
- (1996) Tetrahedron , vol.52 , pp. 6025
- Mansell, H.L.¹

15
- 33845690251
- V. Rodriguez S. M. e E. Pinto C. M. P. Pereira R. C. Braga Quim. Nova 2006 29 1365
- (2006) Quim. Nova , vol.29 , pp. 1365
- Rodriguez, V.¹ Pinto, S.M.E.E.² Pereira, C.M.P.³ Braga, R.C.⁴

16
- 33746873936
- S. L. Schreiber R. E. Claus J. Regan Tetrahedron Lett. 1982 23 3867
- (1982) Tetrahedron Lett. , vol.23 , pp. 3867
- Schreiber, S.L.¹ Claus, R.E.² Regan, J.³

17
- 0034746687
- T. M. Trnka R. H. Grubbs Acc. Chem. Res. 2001 34 18
- (2001) Acc. Chem. Res. , vol.34 , pp. 18
- Trnka, T.M.¹ Grubbs, R.H.²

18
- 0026625425
- The same cascade was also used by Speckamp et al. in their synthesis of anatoxin-a, in that case with a carbomethoxy nitrogen protecting group:
- P. Somfai J. Åhman Tetrahedron Lett. 1992 33 3791
- (1992) Tetrahedron Lett. , vol.33 , pp. 3791
- Somfai, P.¹ Åhman, J.²

19
- 0022517466
- Royer and Husson also used this type of cyclisation promoted by HCl in methanol in the synthesis of ferruginine:
- K. H. Melching H. Hiemstra W. J. Klaver W. N. Speckamp Tetrahedron Lett. 1986 27 4799
- (1986) Tetrahedron Lett. , vol.27 , pp. 4799
- Melching, K.H.¹ Hiemstra, H.² Klaver, W.J.³ Speckamp, W.N.⁴

20
- 0030812254
- These conditions had previously proved problematic to others too: Tanner et al. reported a 51% yield for the HCl-MeOH cyclisation and also observed racemisation of their enantioenriched system, which used a carbomethoxy protecting group and an ethoxyhemiaminal iminium precursor:
- I. Gauthier J. Royer H.-P. Husson J. Org. Chem. 1997 62 6704
- (1997) J. Org. Chem. , vol.62 , pp. 6704
- Gauthier, I.¹ Royer, J.² Husson, H.-P.³

21
- 22144458345
- 2)
- T. Hjelmgaard I. Støtofte D. Tanner J. Org. Chem. 2005 70 5688
- (2005) J. Org. Chem. , vol.70 , pp. 5688
- Hjelmgaard, T.¹ Støtofte, I.² Tanner, D.³

22
- 0033531676
- B. M. Trost J. D. Oslob J. Am. Chem. Soc. 1999 121 3057
- (1999) J. Am. Chem. Soc. , vol.121 , pp. 3057
- Trost, B.M.¹ Oslob, J.D.²

23
- 0034670513
- S. Y. Jonsson C. M. G. Löfström J.-E. Bäckvall J. Org. Chem. 2000 65 8454
- (2000) J. Org. Chem. , vol.65 , pp. 8454
- Jonsson, S.Y.¹ Löfström, C.M.G.² Bäckvall, J.-E.³

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