SCOPUS 정보 검색 플랫폼

Chemistry - A European Journal

Volumn 12, Issue 2, 2005, Pages 568-575

Asymmetric sulfonium ylide mediated cyclopropanation: Stereocontrolled synthesis of (+)-LY354740

(2) Aggarwal, Varinder K a Grange, Emma a

a UNIVERSITY OF BRISTOL (United Kingdom)

Author keywords

Asymmetric synthesis; Cyclopropanation; Diastereoselectivity; LY354740; Sulfur ylides

Indexed keywords

CARBOXYLIC ACIDS; CONCENTRATION (PROCESS); ESTERS; PHARMACODYNAMICS; STOICHIOMETRY;

ASSYMETRIC SYNTHESIS; CYCLOPROPANATION; DIASTEREOSELECTIVITY; LY354740; SULFUR YLIDES;

SULFUR COMPOUNDS;

BICYCLO COMPOUND; CYCLOPENTANE DERIVATIVE; CYCLOPENTENONE; CYCLOPROPANE; CYCLOPROPANE DERIVATIVE; EGLUMETAD; SULFONIUM DERIVATIVE;

ARTICLE; CHEMICAL MODEL; CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

BICYCLO COMPOUNDS; CYCLOPENTANES; CYCLOPROPANES; MODELS, CHEMICAL; STEREOISOMERISM; SULFONIUM COMPOUNDS;

EID: 29544442212 PISSN: 09476539 EISSN: None Source Type: Journal
DOI: 10.1002/chem.200500693 Document Type: Article

Times cited : (83)

References (55)

1
- 0024829451
- G. L. Collingridge, R. A. J. Lester, Pharmacol. Rev. 1989, 41, 143-210.
- (1989) Pharmacol. Rev. , vol.41 , pp. 143-210
- Collingridge, G.L.¹ Lester, R.A.J.²

2
- 0742323781
- G. J. Marek, Curr. Opin. Pharmacol. 2004, 4, 18-22.
- (2004) Curr. Opin. Pharmacol. , vol.4 , pp. 18-22
- Marek, G.J.¹

3
- 15644369847
- J. A. Monn, M. J. Valli, S. M. Massey, R. A. Wright, C. R. Salhoff, B. G. Johnson, T. Howe, C. A. Alt, G. A. Rhodes, R. L. Robey, K. R. Griffey, J. P. Tizzano, M. J. Kallman, D. R. Helton, D. D. Schoepp, J. Med. Chem. 1997, 40, 528-537.
- (1997) J. Med. Chem. , vol.40 , pp. 528-537
- Monn, J.A.¹ Valli, M.J.² Massey, S.M.³ Wright, R.A.⁴ Salhoff, C.R.⁵ Johnson, B.G.⁶ Howe, T.⁷ Alt, C.A.⁸ Rhodes, G.A.⁹ Robey, R.L.¹⁰ Griffey, K.R.¹¹ Tizzano, J.P.¹² Kallman, M.J.¹³ Helton, D.R.¹⁴ Schoepp, D.D.¹⁵

4
- 0031933951
- D. R. Helton, J. P. Tizzano, J. A. Monn, D. D. Schoepp, M. J. Kallman, J. Pharmacol. Exp. Ther. 1998, 284, 651-660.
- (1998) J. Pharmacol. Exp. Ther. , vol.284 , pp. 651-660
- Helton, D.R.¹ Tizzano, J.P.² Monn, J.A.³ Schoepp, D.D.⁴ Kallman, M.J.⁵

5
- 0344980107
- A. Klodzinska, E. Chojnacka-Wojcik, A. Palucha, P. Branski, P. Popik, A. Pilc, Neuropharmacology 1999, 38, 1831-1839.
- (1999) Neuropharmacology , vol.38 , pp. 1831-1839
- Klodzinska, A.¹ Chojnacka-Wojcik, E.² Palucha, A.³ Branski, P.⁴ Popik, P.⁵ Pilc, A.⁶

6
- 0030904243
- A. Bond, J. A. Monn, D. Lodge, NeuroReport 1997, 8, 1463-1466.
- (1997) NeuroReport , vol.8 , pp. 1463-1466
- Bond, A.¹ Monn, J.A.² Lodge, D.³

7
- 0034100686
- A. Shekhar, S. R. Keim, Neuropharmacology 2000, 39, 1139-1146.
- (2000) Neuropharmacology , vol.39 , pp. 1139-1146
- Shekhar, A.¹ Keim, S.R.²

8
- 0035996365
- J. P. Tizzano, K. I. Griffey, D. D. Schoepp, Pharmacol. Biochem. Behav. 2002, 73, 367-374.
- (2002) Pharmacol. Biochem. Behav. , vol.73 , pp. 367-374
- Tizzano, J.P.¹ Griffey, K.I.² Schoepp, D.D.³

9
- 0041488670
- C. Grillon, J. Cordova, L. R. Levine, C. A. Morgan, Psychophamacology 2003, 168, 446-454.
- (2003) Psychophamacology , vol.168 , pp. 446-454
- Grillon, C.¹ Cordova, J.² Levine, L.R.³ Morgan, C.A.⁴

10
- 0141644133
- D. D. Schoepp, R. A. Wright, L. R. Levine, B. Gaydos, W. Z. Potter, Stress 2003, 6, 189-197.
- (2003) Stress , vol.6 , pp. 189-197
- Schoepp, D.D.¹ Wright, R.A.² Levine, L.R.³ Gaydos, B.⁴ Potter, W.Z.⁵

11
- 0038017205
- L. Levine, B. Gaydos, D. Sheehan, A. Goddard, J. Feighner, W. Z. Potter, Schoepp, Neuropharmacology 2002, 43, 77.
- (2002) Neuropharmacology , vol.43 , pp. 77
- Levine, L.¹ Gaydos, B.² Sheehan, D.³ Goddard, A.⁴ Feighner, J.⁵ Potter, W.Z.⁶ Schoepp⁷

12
- 0035996477
- J. C. Gewirtz, A. C. Chen, R. Terwilliger, R. C. Duman, G. J. Marek, Pharmacol. Biochem. Behav. 2002, 73, 317-326.
- (2002) Pharmacol. Biochem. Behav. , vol.73 , pp. 317-326
- Gewirtz, J.C.¹ Chen, A.C.² Terwilliger, R.³ Duman, R.C.⁴ Marek, G.J.⁵

13
- 0033953175
- A. Klodzinska, M. Bijak, E. Chojnacka-Wojcik, B. Kroczka, M. Swiader, S. J. Czuczwar, A. Pilc, Naunyn-Schmiedeberg's Arch. Pharmacol. 2000, 361, 283-288.
- (2000) Naunyn-Schmiedeberg's Arch. Pharmacol. , vol.361 , pp. 283-288
- Klodzinska, A.¹ Bijak, M.² Chojnacka-Wojcik, E.³ Kroczka, B.⁴ Swiader, M.⁵ Czuczwar, S.J.⁶ Pilc, A.⁷

14
- 0034964561
- R. X. Moldrich, M. Jeffrey, A. Talebi, P. M. Beart, A. G. Chapman, B. S. Meldrum, Neuropharmacology 2001, 41, 8-18.
- (2001) Neuropharmacology , vol.41 , pp. 8-18
- Moldrich, R.X.¹ Jeffrey, M.² Talebi, A.³ Beart, P.M.⁴ Chapman, A.G.⁵ Meldrum, B.S.⁶

15
- 0034193374
- S. R. Bradley, M. J. Marino, M. Wittmann, S. T. Rouse, H. Awad, A. I. Levey, P. J. Conn, J. Neurosci. 2000, 20, 3085-3094.
- (2000) J. Neurosci. , vol.20 , pp. 3085-3094
- Bradley, S.R.¹ Marino, M.J.² Wittmann, M.³ Rouse, S.T.⁴ Awad, H.⁵ Levey, A.I.⁶ Conn, P.J.⁷

16
- 0031689603
- J. Konieczny, K. Ossowska, S. Wolfarth, A. Pilc, Naunyn-Schmiedeberg's Arch. Pharmacol. 1998, 358, 500-502.
- (1998) Naunyn-schmiedeberg's Arch. Pharmacol. , vol.358 , pp. 500-502
- Konieczny, J.¹ Ossowska, K.² Wolfarth, S.³ Pilc, A.⁴

17
- 0031704939
- J. H. Woods, J. Clin. Pharmacol. 1998, 38, 773-782.
- (1998) J. Clin. Pharmacol. , vol.38 , pp. 773-782
- Woods, J.H.¹

18
- 0032968641
- J. Vandergriff, K. Rasmussen, Neuropharmacology 1999, 38, 217-222.
- (1999) Neuropharmacology , vol.38 , pp. 217-222
- Vandergriff, J.¹ Rasmussen, K.²

19
- 4143152743
- A. Nakazato, K. Sakagami, A. Yasuhara, H. Ohta, R. Yoshikawa, M. Itoh, M. Nakamura, S. Chaki, J. Med. Chem. 2004, 47, 4570-4587.
- (2004) J. Med. Chem. , vol.47 , pp. 4570-4587
- Nakazato, A.¹ Sakagami, K.² Yasuhara, A.³ Ohta, H.⁴ Yoshikawa, R.⁵ Itoh, M.⁶ Nakamura, M.⁷ Chaki, S.⁸

20
- 7044260863
- F. Zhang, Z. J. Song, D. Tschaen, R. P. Volante, Org. Lett. 2004, 6, 3775-3777.
- (2004) Org. Lett. , vol.6 , pp. 3775-3777
- Zhang, F.¹ Song, Z.J.² Tschaen, D.³ Volante, R.P.⁴

21
- 3042781832
- W. L. Lee, M. J. Miller, J. Org. Chem. 2004, 69, 4516-4519.
- (2004) J. Org. Chem. , vol.69 , pp. 4516-4519
- Lee, W.L.¹ Miller, M.J.²

22
- 4444373880
- N. Yoshikawa, L. S. Tan, N. Yasuda, R. P. Volante, R. D. Tillyer, Tetrahedron Lett. 2004, 45, 7261-7264.
- (2004) Tetrahedron Lett. , vol.45 , pp. 7261-7264
- Yoshikawa, N.¹ Tan, L.S.² Yasuda, N.³ Volante, R.P.⁴ Tillyer, R.D.⁵

23
- 0037863192
- Y. Ohfune, T. Demura, S. Iwama, H. Matsuda, K. Namba, K. Shimamoto, T. Shinada, Tetrahedron Lett. 2003, 44, 5431-5434.
- (2003) Tetrahedron Lett. , vol.44 , pp. 5431-5434
- Ohfune, Y.¹ Demura, T.² Iwama, S.³ Matsuda, H.⁴ Namba, K.⁵ Shimamoto, K.⁶ Shinada, T.⁷

24
- 0036132202
- C. Pedregal, W. Prowse, Bioorg. Med. Chem. 2002, 10, 433-436.
- (2002) Bioorg. Med. Chem. , vol.10 , pp. 433-436
- Pedregal, C.¹ Prowse, W.²

25
- 0034649605
- A. Nakazato, T. Kumagai, K. Sakagami, R. Yoshikawa, Y. Suzuki, S. Chaki, H. Ito, T. Taguchi, S. Nakanishi, S. Okuyama, J. Med. Chem. 2000, 43, 4893-4909.
- (2000) J. Med. Chem. , vol.43 , pp. 4893-4909
- Nakazato, A.¹ Kumagai, T.² Sakagami, K.³ Yoshikawa, R.⁴ Suzuki, Y.⁵ Chaki, S.⁶ Ito, H.⁷ Taguchi, T.⁸ Nakanishi, S.⁹ Okuyama, S.¹⁰

26
- 0033602516
- J. A. Monn, M. J. Valli, S. M. Massey, M. M. Hansen, T. J. Kress, J. P. Wepsiec, A. R. Harkness, J. L. Grutsch, R. A. Wright, B. G. Johnson, S. L. Andis, A. Kingston, R. Tomlinson, R. Lewis, K. R. Griffey, J. P. Tizzano, D. D. Schoepp, J. Med. Chem. 1999, 42, 1027-1040.
- (1999) J. Med. Chem. , vol.42 , pp. 1027-1040
- Monn, J.A.¹ Valli, M.J.² Massey, S.M.³ Hansen, M.M.⁴ Kress, T.J.⁵ Wepsiec, J.P.⁶ Harkness, A.R.⁷ Grutsch, J.L.⁸ Wright, R.A.⁹ Johnson, B.G.¹⁰ Andis, S.L.¹¹ Kingston, A.¹² Tomlinson, R.¹³ Lewis, R.¹⁴ Griffey, K.R.¹⁵ Tizzano, J.P.¹⁶ Schoepp, D.D.¹⁷

27
- 0030602196
- E. D. Moher, Tetrahedron Lett. 1996, 37, 8637-8640.
- (1996) Tetrahedron Lett. , vol.37 , pp. 8637-8640
- Moher, E.D.¹

28
- 0031585109
- I. Collado, C. Dominguez, J. Ezquerra, C. Pedregal, J. A. Monn, Tetrahedron Lett. 1997, 38, 2133-2136.
- (1997) Tetrahedron Lett. , vol.38 , pp. 2133-2136
- Collado, I.¹ Dominguez, C.² Ezquerra, J.³ Pedregal, C.⁴ Monn, J.A.⁵

29
- 0031579430
- C. Dominguez, J. Ezquerra, L. Prieto, M. Espada, C. Pedregal, Tetrahedron: Asymmetry 1997, 8, 511-514.
- (1997) Tetrahedron: Asymmetry , vol.8 , pp. 511-514
- Dominguez, C.¹ Ezquerra, J.² Prieto, L.³ Espada, M.⁴ Pedregal, C.⁵

30
- 0032506565
- C. Dominguez, J. Ezquerra, S. R. Baker, S. Borrelly, L. Prieto, M. Espada, C. Pedregal, Tetrahedron Lett. 1998, 39, 9305-9308.
- (1998) Tetrahedron Lett. , vol.39 , pp. 9305-9308
- Dominguez, C.¹ Ezquerra, J.² Baker, S.R.³ Borrelly, S.⁴ Prieto, L.⁵ Espada, M.⁶ Pedregal, C.⁷

31
- 0036775427
- M. G. Moloney, Nat. Prod. Rep. 2002, 19, 597-616.
- (2002) Nat. Prod. Rep. , vol.19 , pp. 597-616
- Moloney, M.G.¹

32
- 20844441772
- C. Dominguez, L. Prieto, M. J. Valli, S. M. Massey, M. Bures, R. A. Wright, B. G. Johnson, S. L. Andis, A. Kingston, D. D. Schoepp, J. A. Monn, J. Med. Chem. 2005, 48, 3605-3612.
- (2005) J. Med. Chem. , vol.48 , pp. 3605-3612
- Dominguez, C.¹ Prieto, L.² Valli, M.J.³ Massey, S.M.⁴ Bures, M.⁵ Wright, R.A.⁶ Johnson, B.G.⁷ Andis, S.L.⁸ Kingston, A.⁹ Schoepp, D.D.¹⁰ Monn, J.A.¹¹

33
- 4143093678
- V. K. Aggarwal, C. L. Winn, Acc. Chem. Res. 2004, 37, 611-620.
- (2004) Acc. Chem. Res. , vol.37 , pp. 611-620
- Aggarwal, V.K.¹ Winn, C.L.²

34
- 0041733341
- V. K. Aggarwal, E. Alonso, I. Bae, G. Hynd, K. M. Lydon, M. J. Palmer, M. Patel, M. Porcelloni, J. Richardson, R. A. Stenson, J. R. Studley, J. L. Vasse, C. L. Winn, J. Am. Chem. Soc. 2003, 125, 10926-10940.
- (2003) J. Am. Chem. Soc. , vol.125 , pp. 10926-10940
- Aggarwal, V.K.¹ Alonso, E.² Bae, I.³ Hynd, G.⁴ Lydon, K.M.⁵ Palmer, M.J.⁶ Patel, M.⁷ Porcelloni, M.⁸ Richardson, J.⁹ Stenson, R.A.¹⁰ Studley, J.R.¹¹ Vasse, J.L.¹² Winn, C.L.¹³

35
- 0242525164
- V. K. Aggarwal, J. Richardson, Chem. Commun. 2003, 2644-2651.
- (2003) Chem. Commun. , pp. 2644-2651
- Aggarwal, V.K.¹ Richardson, J.²

36
- 0000817736
- V. K. Aggarwal, E. Alonso, G. Hynd, K. M. Lydon, M. J. Palmer, M. Porcelloni, J. R. Studley, Angew. Chem. 2001, 113, 1479-1482;
- (2001) Angew. Chem. , vol.113 , pp. 1479-1482
- Aggarwal, V.K.¹ Alonso, E.² Hynd, G.³ Lydon, K.M.⁴ Palmer, M.J.⁵ Porcelloni, M.⁶ Studley, J.R.⁷

37
- 0035901657
- Angew. Chem. Int. Ed. 2001, 40, 1430-1433.
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1430-1433

38
- 0032569215
- V. K. Aggarwal, J. G. Ford, S. Fonquerna, H. Adams, R. V. H. Jones, R. Fieldhouse, J. Am. Chem. Soc. 1998, 120, 8328-8339.
- (1998) J. Am. Chem. Soc. , vol.120 , pp. 8328-8339
- Aggarwal, V.K.¹ Ford, J.G.² Fonquerna, S.³ Adams, H.⁴ Jones, R.V.H.⁵ Fieldhouse, R.⁶

39
- 0029900606
- V. K. Aggarwal, J. G. Ford, A. Thompson, R. V. H. Jones, M. C. H. Standen, J. Am. Chem. Soc. 1996, 118, 7004-7005.
- (1996) J. Am. Chem. Soc. , vol.118 , pp. 7004-7005
- Aggarwal, V.K.¹ Ford, J.G.² Thompson, A.³ Jones, R.V.H.⁴ Standen, M.C.H.⁵

40
- 0002086027
- V. K. Aggarwal, Synlett 1998, 329-336.
- (1998) Synlett , pp. 329-336
- Aggarwal, V.K.¹

41
- 0001334291
- V. K. Aggarwal, A. Thompson, R. V. H. Jones, M. C. H. Standen, J. Org. Chem. 1996, 61, 8368-8369.
- (1996) J. Org. Chem. , vol.61 , pp. 8368-8369
- Aggarwal, V.K.¹ Thompson, A.² Jones, R.V.H.³ Standen, M.C.H.⁴

42
- 0000799953
- V. K. Aggarwal, E. Alonso, G. Y. Fang, M. Ferrara, G. Hynd, M. Porcelloni, Angew. Chem. 2001, 113, 1482-1485;
- (2001) Angew. Chem. , vol.113 , pp. 1482-1485
- Aggarwal, V.K.¹ Alonso, E.² Fang, G.Y.³ Ferrara, M.⁴ Hynd, G.⁵ Porcelloni, M.⁶

43
- 0035901642
- Angew. Chem. Int. Ed. 2001, 40, 1433-1436.
- (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 1433-1436

44
- 0034619269
- V. K. Aggarwal, H. W. Smith, G. Hynd, R. V. H. Jones, R. Fieldhouse, S. E. Spey, J. Chem. Soc. Perkin Trans. 1 2000, 3267-3276.
- (2000) J. Chem. Soc. Perkin Trans. 1 , pp. 3267-3276
- Aggarwal, V.K.¹ Smith, H.W.² Hynd, G.³ Jones, R.V.H.⁴ Fieldhouse, R.⁵ Spey, S.E.⁶

45
- 33947337893
- G. B. Payne, J. Org. Chem. 1967, 32, 3351-3355.
- (1967) J. Org. Chem. , vol.32 , pp. 3351-3355
- Payne, G.B.¹

46
- 29544452937
- note
- The cyclopropanation of enones 25 and 26 with preformed ylides 8 and 19 gave low diastereoselectivity (2:1 and 1:1, respectively).

47
- 0036009485
- N. Ohmori, J. Chem. Soc. Perkin Trans. 1 2002, 755-767.
- (2002) J. Chem. Soc. Perkin Trans. 1 , pp. 755-767
- Ohmori, N.¹

48
- 4444251750
- J. L. G. Ruano, C. Fajardo, M. R. Martin, W. Midura, M. Mikolajczyk, Tetrahedron: Asymmetry 2004, 15, 2475-2482.
- (2004) Tetrahedron: Asymmetry , vol.15 , pp. 2475-2482
- Ruano, J.L.G.¹ Fajardo, C.² Martin, M.R.³ Midura, W.⁴ Mikolajczyk, M.⁵

49
- 0000504753
- P. A. Wender, C. L. Hillemann, M. J. Szymonifka, Tetrahedron Lett. 1980, 21, 2205-2208.
- (1980) Tetrahedron Lett. , vol.21 , pp. 2205-2208
- Wender, P.A.¹ Hillemann, C.L.² Szymonifka, M.J.³

50
- 0033593515
- R. Zhang, A. Mamai, J. S. Madalengoitia, J. Org. Chem. 1999, 64, 547-555.
- (1999) J. Org. Chem. , vol.64 , pp. 547-555
- Zhang, R.¹ Mamai, A.² Madalengoitia, J.S.³

51
- 0000663810
- D. Romo, A. I. Meyers, J. Org. Chem. 1992, 57, 6265-6270.
- (1992) J. Org. Chem. , vol.57 , pp. 6265-6270
- Romo, D.¹ Meyers, A.I.²

52
- 29544441498
- note
- We also tested ylide 23 with cyclopentenone, but obtained no cyclopropanes. Use of amide-stabilized ylides 27 and 28 did produce cyclopropanes, but again with 1:1 diastereoselectivity.

53
- 6044272653
- C. D. Papageorgiou, M. A. C. de Dios, S. V. Ley, M. J. Gaunt, Angew. Chem. 2004, 116, 4741-4744;
- (2004) Angew. Chem. , vol.116 , pp. 4741-4744
- Papageorgiou, C.D.¹ De Dios, M.A.C.² Ley, S.V.³ Gaunt, M.J.⁴

54
- 5344280509
- Angew. Chem. Int. Ed. 2004, 43, 4641-4644.
- (2004) Angew. Chem. Int. Ed. , vol.43 , pp. 4641-4644

55
- 0010453368
- B. M. Trost, J. Am. Chem. Soc. 1967, 89, 138.
- (1967) J. Am. Chem. Soc. , vol.89 , pp. 138
- Trost, B.M.¹

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