SCOPUS 정보 검색 플랫폼

Organic and Biomolecular Chemistry

Volumn 5, Issue 21, 2007, Pages 3544-3553

Asymmetric synthesis of 3-amino-4-hydroxy-2-(hydroxymethyl)pyrrolidines as potential glycosidase inhibitors

(4) Curtis, Kim L a Evinson, Emma L b Handa, Sandeep a Singh, Kuldip a

a UNIVERSITY OF LEICESTER (United Kingdom)

b Molecular Nature Ltd (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC POLYMERS; ENZYME INHIBITION; FUNCTIONAL GROUPS; HYDROXYLATION; ISOMERS; REACTION KINETICS; STEREOSELECTIVITY;

AMINO PYRROLIDINES; AMINOHYDROXYLATION; GLYCOSIDASE INHIBITORS;

SYNTHESIS (CHEMICAL);

ALPHA GALACTOSIDASE; BETA GALACTOSIDASE; ENZYME INHIBITOR; GLYCOSIDASE; PYRROLIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; HYDROXYLATION; STEREOISOMERISM; SYNTHESIS;

ALPHA-GALACTOSIDASE; BETA-GALACTOSIDASE; ENZYME INHIBITORS; GLYCOSIDE HYDROLASES; HYDROXYLATION; MOLECULAR STRUCTURE; PYRROLIDINES; STEREOISOMERISM;

EID: 35348917610 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/b711994a Document Type: Article

Times cited : (21)

References (49)

1
- 33748708627
- E. B. de Melo A. D. Gomes I. Carvalho Tetrahedron 2006 62 10277
- (2006) Tetrahedron , vol.62 , pp. 10277
- De Melo, E.B.¹ Gomes, A.D.² Carvalho, I.³

2
- 0036462605
- V. H. Lillelund H. H. Jensen X. F. Liang M. Bols Chem. Rev. 2002 102 515
- (2002) Chem. Rev. , vol.102 , pp. 515
- Lillelund, V.H.¹ Jensen, H.H.² Liang, X.F.³ Bols, M.⁴

3
- 0033559148
- T. D. Heihtman A. T. Vasella Angew. Chem., Int. Ed. 1999 38 750
- (1999) Angew. Chem., Int. Ed. , vol.38 , pp. 750
- Heihtman, T.D.¹ Vasella, A.T.²

4
- 0034607947
- N. Asano R. J. Nash R. J. Molyneux G. W. J. Fleet Tetrahedron: Asymmetry 2000 11 1645
- (2000) Tetrahedron: Asymmetry , vol.11 , pp. 1645
- Asano, N.¹ Nash, R.J.² Molyneux, R.J.³ Fleet, G.W.J.⁴

5
- 0242287992
- N. Asano Glycobiology 2003 13 93R
- (2003) Glycobiology , vol.13
- Asano, N.¹

6
- 0035925104
- A. A. Watson G. W. J. Fleet N. Asano R. J. Molyneux R. J. Nash Phytochemistry 2001 56 265
- (2001) Phytochemistry , vol.56 , pp. 265
- Watson, A.A.¹ Fleet, G.W.J.² Asano, N.³ Molyneux, R.J.⁴ Nash, R.J.⁵

7
- 33748661509
- S. Gerber-Lemaire L. Juillerat-Jeanneret Mini-Rev. Med. Chem. 2006 6 1043
- (2006) Mini-Rev. Med. Chem. , vol.6 , pp. 1043
- Gerber-Lemaire, S.¹ Juillerat-Jeanneret, L.²

8
- 0003532642
- Wiley VCH, Weinheim
- A. E. Stütz, in Iminosugars as Glycosidase Inhibitors: Nojirimycin and Beyond, Wiley VCH, Weinheim, 1999
- (1999) Iminosugars as Glycosidase Inhibitors: Nojirimycin and beyond
- Stütz In, A.E.¹

9
- 0001659751
- G. W. J. Fleet S. J. Nicholas P. W. Smith S. V. Evans L. E. Fellows R. J. Nash Tetrahedron Lett. 1985 26 3127
- (1985) Tetrahedron Lett. , vol.26 , pp. 3127
- Fleet, G.W.J.¹ Nicholas, S.J.² Smith, P.W.³ Evans, S.V.⁴ Fellows, L.E.⁵ Nash, R.J.⁶

10
- 0035903867
- F. Popowycz S. Gerber-Lemaire R. Demange E. Rodriguez-Garcia A. T. C. Asenjo I. Robina P. Vogel Bioorg. Med. Chem. Lett. 2001 11 2489
- (2001) Bioorg. Med. Chem. Lett. , vol.11 , pp. 2489
- Popowycz, F.¹ Gerber-Lemaire, S.² Demange, R.³ Rodriguez-Garcia, E.⁴ Asenjo, A.T.C.⁵ Robina, I.⁶ Vogel, P.⁷

11
- 0036180550
- For selected examples see:
- K. Yasuda H. Kizu T. Yamashita Y. Kameda A. Kato R. J. Nash G. W. J. Fleet R. J. Molyneux N. Asano J. Nat. Prod. 2002 65 198
- (2002) J. Nat. Prod. , vol.65 , pp. 198
- Yasuda, K.¹ Kizu, H.² Yamashita, T.³ Kameda, Y.⁴ Kato, A.⁵ Nash, R.J.⁶ Fleet, G.W.J.⁷ Molyneux, R.J.⁸ Asano, N.⁹

12
- 33646493353
- C. Laroche J.-B. Behr J. Szymoniak P. Bertus C. Schütz P. Vogel R. Plantier-Royona Bioorg. Med. Chem. 2006 14 4047
- (2006) Bioorg. Med. Chem. , vol.14 , pp. 4047
- Laroche, C.¹ Behr, J.-B.² Szymoniak, J.³ Bertus, P.⁴ Schütz, C.⁵ Vogel, P.⁶ Plantier-Royona, R.⁷

13
- 23944457624
- J. H. Kim M. J. Curtis-Long W. D. Seo J. H. Lee B. W. Lee Y. J. Yoon K. Y. Kanga K. H. Parka Bioorg. Med. Chem. Lett. 2005 15 4282
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 4282
- Kim, J.H.¹ Curtis-Long, M.J.² Seo, W.D.³ Lee J., H.⁴ Lee B., W.⁵ Yoon, Y.J.⁶ Kanga, K.Y.⁷ Parka, K.H.⁸

14
- 2542511633
- N. Asano K. Ikeda M. Kasahara Y. Arai H. Kizu J. Nat. Prod. 2004 67 846
- (2004) J. Nat. Prod. , vol.67 , pp. 846
- Asano, N.¹ Ikeda, K.² Kasahara, M.³ Arai, Y.⁴ Kizu, H.⁵

15
- 0042305005
- F. Popowycz S. Gerber-Lemaire E. Rodriguez-Garcia C. Shütz P. Vogel Helv. Chim. Acta 2003 86 1914
- (2003) Helv. Chim. Acta , vol.86 , pp. 1914
- Popowycz, F.¹ Gerber-Lemaire, S.² Rodriguez-Garcia, E.³ Shütz, C.⁴ Vogel, P.⁵

16
- 0036903709
- S. Gerber-Lemaire F. Popowycz E. Rodriguez-Garcia A. T. C. Asenjo I. Robina P. Vogel ChemBioChem 2002 3 466
- (2002) ChemBioChem , vol.3 , pp. 466
- Gerber-Lemaire, S.¹ Popowycz, F.² Rodriguez-Garcia, E.³ Asenjo, A.T.C.⁴ Robina, I.⁵ Vogel, P.⁶

17
- 33646441081
- H. Fiaux C. Schütz P. Vogel L. Juillerat-Jeanneret S. Gerber-Lemaire Chimia 2006 60 185
- (2006) Chimia , vol.60 , pp. 185
- Fiaux, H.¹ Schütz, C.² Vogel, P.³ Juillerat-Jeanneret, L.⁴ Gerber-Lemaire, S.⁵

18
- 33947207008
- S. Favre H. Fiaux C. Schütz P. Vogel L. Juillerat-Jeanneret S. Gerber-Lemaire Heterocycles 2006 69 179
- (2006) Heterocycles , vol.69 , pp. 179
- Favre, S.¹ Fiaux, H.² Schütz, C.³ Vogel, P.⁴ Juillerat-Jeanneret, L.⁵ Gerber-Lemaire, S.⁶

19
- 0029932154
- D. Kim Y. Kim T. Kim K. H. Kim Bioorg. Med. Chem. Lett. 1996 6 643
- (1996) Bioorg. Med. Chem. Lett. , vol.6 , pp. 643
- Kim, D.¹ Kim, Y.² Kim, T.³ Kim, K.H.⁴

20
- 0030812235
- C. Herdeis A. Aschenbrenner A. Kirfel F. Schwabenlander Tetrahedron: Asymmetry 1997 8 2421
- (1997) Tetrahedron: Asymmetry , vol.8 , pp. 2421
- Herdeis, C.¹ Aschenbrenner, A.² Kirfel, A.³ Schwabenlander, F.⁴

21
- 0032907265
- G. Limberg I. Lundt J. Zavilla Synthesis 1999 178
- (1999) Synthesis , pp. 178
- Limberg, G.¹ Lundt, I.² Zavilla, J.³

22
- 0025061532
- L. Czollner J. Kuszmann A. Vasella Helv. Chim. Acta 1990 73 1338
- (1990) Helv. Chim. Acta , vol.73 , pp. 1338
- Czollner, L.¹ Kuszmann, J.² Vasella, A.³

23
- 0033593493
- E. Falb Y. Bechor A. Nudelman A. Hassner A. Albexk H. E. Gottlieb J. Org. Chem. 1999 64 498
- (1999) J. Org. Chem. , vol.64 , pp. 498
- Falb, E.¹ Bechor, Y.² Nudelman, A.³ Hassner, A.⁴ Albexk, A.⁵ Gottlieb, H.E.⁶

24
- 84988053632
- C. Palomo P. C. Fernando C. Cuevas J. M. Ontoria J. M. Odriozola S. Munt Bull. Soc. Chim. Belg. 1992 101 541
- (1992) Bull. Soc. Chim. Belg. , vol.101 , pp. 541
- Palomo, C.¹ Fernando, P.C.² Cuevas, C.³ Ontoria, J.M.⁴ Odriozola, J.M.⁵ Munt, S.⁶

25
- 0032576830
- J. K. Robinson V. Lee T. D. W. Claridge J. E. Baldwin C. J. Schofield Tetrahedron 1998 54 981
- (1998) Tetrahedron , vol.54 , pp. 981
- Robinson, J.K.¹ Lee, V.² Claridge, T.D.W.³ Baldwin, J.E.⁴ Schofield, C.J.⁵

26
- 21844445603
- K. L. Curtis J. Fawcett S. Handa Tetrahedron Lett. 2005 46 5297
- (2005) Tetrahedron Lett. , vol.46 , pp. 5297
- Curtis, K.L.¹ Fawcett, J.² Handa, S.³

27
- 0037032268
- T. J. Donohoe P. D. Johnson A. Cowley M. Keenan J. Am. Chem. Soc. 2002 124 12934
- (2002) J. Am. Chem. Soc. , vol.124 , pp. 12934
- Donohoe, T.J.¹ Johnson, P.D.² Cowley, A.³ Keenan, M.⁴

28
- 0141940660
- T. J. Donohoe P. D. Johnson R. Pye Org. Biomol. Chem. 2003 2025
- (2003) Org. Biomol. Chem. , pp. 2025
- Donohoe, T.J.¹ Johnson, P.D.² Pye, R.³

29
- 4043171449
- T. J. Donohoe P. D. Johnson R. Pye M. Keenan Org. Lett. 2004 6 2583
- (2004) Org. Lett. , vol.6 , pp. 2583
- Donohoe, T.J.¹ Johnson, P.D.² Pye, R.³ Keenan, M.⁴

30
- 0032578672
- N. B. Westwood R. T. Walker Tetrahedron 1998 54 13391
- (1998) Tetrahedron , vol.54 , pp. 13391
- Westwood, N.B.¹ Walker, R.T.²

31
- 0001388469
- T. Ibuka T. Taga H. Habashita K. Nakai H. Tamamura F. Nobutaka C. Yukiyasu N. Hisao Y. Yoshinori J. Org. Chem. 1993 58 1207
- (1993) J. Org. Chem. , vol.58 , pp. 1207
- Ibuka, T.¹ Taga, T.² Habashita, H.³ Nakai, K.⁴ Tamamura, H.⁵ Nobutaka, F.⁶ Yukiyasu, C.⁷ Hisao, N.⁸ Yoshinori, Y.⁹

32
- 0037155707
- F. Busqé P. de March M. Figueredo J. Font T. Gallagher S. Milan Tetrahedron: Asymmetry 2002 13 437
- (2002) Tetrahedron: Asymmetry , vol.13 , pp. 437
- Busqé, F.¹ De March, P.² Figueredo, M.³ Font, J.⁴ Gallagher, T.⁵ Milan, S.⁶

33
- 33847625071
- J. L. Cohen A. R. Chamberlin Tetrahedron Lett. 2007 48 2533
- (2007) Tetrahedron Lett. , vol.48 , pp. 2533
- Cohen, J.L.¹ Chamberlin, A.R.²

34
- 33644653551
- T. J. Donohoe M. J. Chughtai D. J. Klauber D. Griffin A. D. Campbell J. Am. Chem. Soc. 2006 128 2514
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 2514
- Donohoe, T.J.¹ Chughtai, M.J.² Klauber, D.J.³ Griffin, D.⁴ Campbell, A.D.⁵

35
- 4143087960
- M. N. Kenworthy G. D. McAllister R. J. K. Taylor Tetrahedron Lett. 2004 45 6661
- (2004) Tetrahedron Lett. , vol.45 , pp. 6661
- Kenworthy, M.N.¹ McAllister, G.D.² Taylor, R.J.K.³

36
- 14544306449
- A more efficient version of the TA reaction has now been developed: see reference 20b and also:
- M. N. Kenworthy R. J. K. Taylor Org. Biomol. Chem. 2005 603
- (2005) Org. Biomol. Chem. , pp. 603
- Kenworthy, M.N.¹ Taylor, R.J.K.²

37
- 34248375267
- T. J. Donohoe C. J. R. Bataille W. Gattrell J. Kloesges E. Rossignol Org. Lett. 2007 9 1725
- (2007) Org. Lett. , vol.9 , pp. 1725
- Donohoe, T.J.¹ Bataille, C.J.R.² Gattrell, W.³ Kloesges, J.⁴ Rossignol, E.⁵

38
- 0037144679
- J. R. Dehli V. J. Gotor J. Org. Chem. 2002 67 6816
- (2002) J. Org. Chem. , vol.67 , pp. 6816
- Dehli, J.R.¹ Gotor, V.J.²

39
- 35348821110
- A similar intramolecular epoxide ring-opening strategy has recently been reported:
- C. B. Hudson A. V. Robertson W. R. J. Simpson Aust. J. Chem. 1975 28 274
- (1975) Aust. J. Chem. , vol.28 , pp. 274
- Hudson, C.B.¹ Robertson, A.V.² Simpson, W.R.J.³

40
- 13944278392
- Y. Wang A. Benn N. Flinn T. Monk M. Ramjee J. Watts M. Quibell Bioorg. Med. Chem. Lett. 2005 15 1327
- (2005) Bioorg. Med. Chem. Lett. , vol.15 , pp. 1327
- Wang, Y.¹ Benn, A.² Flinn, N.³ Monk, T.⁴ Ramjee, M.⁵ Watts, J.⁶ Quibell, M.⁷

41
- 0025240645
- J. D. Aebi D. T. Deyo C. Sun D. Guillaume B. Dunlap D. H. Rich J. Med. Chem. 1990 33 999
- (1990) J. Med. Chem. , vol.33 , pp. 999
- Aebi, J.D.¹ Deyo, D.T.² Sun, C.³ Guillaume, D.⁴ Dunlap, B.⁵ Rich, D.H.⁶

42
- 0029848266
- L. F. Garcia-Alles J. Magdalena V. Gotor J. Org. Chem. 1996 61 6980
- (1996) J. Org. Chem. , vol.61 , pp. 6980
- Garcia-Alles, L.F.¹ Magdalena, J.² Gotor, V.³

43
- 0027477930
- M. Yamamoto M. Suzuki K. Kishikawa S. Kohmoto Synthesis 1993 307
- (1993) Synthesis , pp. 307
- Yamamoto, M.¹ Suzuki, M.² Kishikawa, K.³ Kohmoto, S.⁴

44
- 0025000890
- S. Knapp P. J. Kukkola S. Sharma T. G. M. Dhar A. B. J. Naughton J. Org. Chem. 1990 55 5700
- (1990) J. Org. Chem. , vol.55 , pp. 5700
- Knapp, S.¹ Kukkola, P.J.² Sharma, S.³ Dhar, T.G.M.⁴ Naughton, A.B.J.⁵

45
- 0000692017
- C. Bachand H. Driguez J. M. Paton D. Touchard J. Lessard J. Org. Chem. 1974 39 3136
- (1974) J. Org. Chem. , vol.39 , pp. 3136
- Bachand, C.¹ Driguez, H.² Paton, J.M.³ Touchard, D.⁴ Lessard, J.⁵

46
- 0027504458
- Y. Morizawa T. Nakayama Y. Matsumura K. Uchida A. Yasuda Bull. Chem. Soc. Jpn. 1993 66 2714
- (1993) Bull. Chem. Soc. Jpn. , vol.66 , pp. 2714
- Morizawa, Y.¹ Nakayama, T.² Matsumura, Y.³ Uchida, K.⁴ Yasuda, A.⁵

47
- 0011213172
- G. Buchanan K. W. Lumbard R. J. Sturgeon D. K. Thompson R. H. Wightman J. Chem. Soc., Perkin Trans. 1 1990 699
- (1990) J. Chem. Soc., Perkin Trans. 1 , pp. 699
- Buchanan, G.¹ Lumbard, K.W.² Sturgeon, R.J.³ Thompson, D.K.⁴ Wightman, R.H.⁵

48
- 0001567161
- Y. Ryu G. Kim J. Org. Chem. 1995 60 103
- (1995) J. Org. Chem. , vol.60 , pp. 103
- Ryu, Y.¹ Kim, G.²

49
- 0004055425
- Pergamon Press, NY, 3rd edn
- D. D. Penin and W. L. F. Armarego, Purification of Laboratory Chemicals, Pergamon Press, NY, 3rd edn, 1988
- (1988) Purification of Laboratory Chemicals
- Penin, D.D.¹ Armarego, W.L.F.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.