SCOPUS 정보 검색 플랫폼

Organic and Biomolecular Chemistry

Volumn 9, Issue 3, 2011, Pages 758-764

Stereoselective synthesis of the C15-C26 fragment of the antitumor agent (-)-dictyostatin

(5) Ferreiro Mederos, Leticia a,b Vila Gisbert, Silvia a Urbano, Antonio a Carreño, M Carmen a Colobert, Franoise b

a UNIVERSIDAD AUTÓNOMA DE MADRID (Spain)

b UNIVERSITÉ DE STRASBOURG (France)

Author keywords

[No Author keywords available]

Indexed keywords

ANTI-TUMOR AGENTS; DICTYOSTATIN; REFORMATSKY-TYPE REACTIONS; STEREO-SELECTIVE; STEREOSELECTIVE SYNTHESIS;

STEREOSELECTIVITY;

SYNTHESIS (CHEMICAL);

ANTINEOPLASTIC AGENT; DICTYOSTATIN; MACROLIDE;

ARTICLE; CHEMICAL STRUCTURE; STEREOISOMERISM; SYNTHESIS;

ANTINEOPLASTIC AGENTS; MACROLIDES; MOLECULAR STRUCTURE; STEREOISOMERISM;

EID: 79251508381 PISSN: 14770520 EISSN: None Source Type: Journal
DOI: 10.1039/c0ob00491j Document Type: Article

Times cited : (9)

References (57)

1
- 0028364041
- G. R. Pettit Z. A. Cichacz F. Gao M. R. Boyd J. M. Schmidt J. Chem. Soc., Chem. Commun. 1994 1111 1112
- (1994) J. Chem. Soc., Chem. Commun. , pp. 1111-1112
- Pettit, G.R.¹ Cichacz, Z.A.² Gao, F.³ Boyd, M.R.⁴ Schmidt, J.M.⁵

2
- 0038005594
- R. A. Isbrucker J. Cummins S. A. Pomponi R. E. Longley A. E. Wright Biochem. Pharmacol. 2003 66 75 82
- (2003) Biochem. Pharmacol. , vol.66 , pp. 75-82
- Isbrucker, R.A.¹ Cummins, J.² Pomponi, S.A.³ Longley, R.E.⁴ Wright, A.E.⁵

3
- 1842431809
- I. Paterson R. Britton O. Delgado A. Wright Chem. Commun. 2004 632 633
- (2004) Chem. Commun. , pp. 632-633
- Paterson, I.¹ Britton, R.² Delgado, O.³ Wright, A.⁴

4
- 5344236083
- I. Paterson R. Britton O. Delgado A. Meyer K. G. Poullennec Angew. Chem., Int. Ed. 2004 43 4629 4633
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 4629-4633
- Paterson, I.¹ Britton, R.² Delgado, O.³ Meyer, A.⁴ Poullennec, K.G.⁵

5
- 5344247972
- Y. Shin J. Fournier Y. Fukui A. M. Bruckner D. P. Curran Angew. Chem., Int. Ed. 2004 43 4634 4637
- (2004) Angew. Chem., Int. Ed. , vol.43 , pp. 4634-4637
- Shin, Y.¹ Fournier, J.² Fukui, Y.³ Bruckner, A.M.⁴ Curran, D.P.⁵

6
- 53849091740
- A. Canales R. Matesanz N. M. Gardner J. M. Andreu I. Paterson J. F. Díaz J. Jímenez-Barbero Chem.-Eur. J. 2008 14 7557 7569
- (2008) Chem.-Eur. J. , vol.14 , pp. 7557-7569
- Canales, A.¹ Matesanz, R.² Gardner, N.M.³ Andreu, J.M.⁴ Paterson, I.⁵ Díaz, J.F.⁶ Jímenez-Barbero, J.⁷

7
- 27744476031
- C. Madiraju M. C. Edler E. Hamel B. S. Raccor G. Zhu A. Vogt Y. Shin J. Fournier Y. Fukui A. M. Bruckner D. P. Curran B. W. Day Biochemistry 2005 44 15053 15063
- (2005) Biochemistry , vol.44 , pp. 15053-15063
- Madiraju, C.¹ Edler, M.C.² Hamel, E.³ Raccor, B.S.⁴ Zhu, G.⁵ Vogt, A.⁶ Shin, Y.⁷ Fournier, J.⁸ Fukui, Y.⁹ Bruckner, A.M.¹⁰ Curran, D.P.¹¹ Day, B.W.¹²

8
- 69249101271
- I. Paterson G. J. Florence Topics in Current Chemistry 2009 286 73 119
- (2009) Topics in Current Chemistry , vol.286 , pp. 73-119
- Paterson, I.¹ Florence, G.J.²

9
- 69249146553
- B. Pfeiffer C. N. Kuzniewski C. Wullschleger K.-H. Altmann Topics in Current Chemistry 2009 286 1 72
- (2009) Topics in Current Chemistry , vol.286 , pp. 1-72
- Pfeiffer, B.¹ Kuzniewski, C.N.² Wullschleger, C.³ Altmann, K.-H.⁴

10
- 41749125906
- G. J. Florence N. M. Gardner I. Paterson Nat. Prod. Rep. 2008 25 342 375
- (2008) Nat. Prod. Rep. , vol.25 , pp. 342-375
- Florence, G.J.¹ Gardner, N.M.² Paterson, I.³

11
- 77955653152
- See reference 4 and the following: I. Paterson R. Britton O. Delgado N. M. Gardner A. Meyer G. J. Naylor K. G. Poullennec Tetrahedron 2010 66 6534 6545
- (2010) Tetrahedron , vol.66 , pp. 6534-6545
- Paterson, I.¹ Britton, R.² Delgado, O.³ Gardner, N.M.⁴ Meyer, A.⁵ Naylor, G.J.⁶ Poullennec, K.G.⁷

12
- 77954300312
- W. Zhu M. Jimenez W.-H. Jung D. P. Camarco R. Balachandran A. Vogt B. W. Day D. P. Curran J. Am. Chem. Soc. 2010 132 9175 9187
- (2010) J. Am. Chem. Soc. , vol.132 , pp. 9175-9187
- Zhu, W.¹ Jimenez, M.² Jung, W.-H.³ Camarco, D.P.⁴ Balachandran, R.⁵ Vogt, A.⁶ Day, B.W.⁷ Curran, D.P.⁸

13
- 34347263634
- Y. Shin J.-H. Fournier A. Brueckner Ch. Madiraju R. Balachandran B. S. Raccor M. C. Edler E. Hamel R. P. Sikorski A. Vogt B. W. Day D. P. Curran Tetrahedron 2007 63 8537 8562
- (2007) Tetrahedron , vol.63 , pp. 8537-8562
- Shin, Y.¹ Fournier, J.-H.² Brueckner, A.³ Madiraju, Ch.⁴ Balachandran, R.⁵ Raccor, B.S.⁶ Edler, M.C.⁷ Hamel, E.⁸ Sikorski, R.P.⁹ Vogt, A.¹⁰ Day, B.W.¹¹ Curran, D.P.¹²

14
- 33846418752
- P. V. Ramachandran A. Srivastava D. Hazra Org. Lett. 2007 9 157 160
- (2007) Org. Lett. , vol.9 , pp. 157-160
- Ramachandran, P.V.¹ Srivastava, A.² Hazra, D.³

15
- 33646453676
- G. W. O'Neil A. Phillips J. Am. Chem. Soc. 2006 128 5340 5341
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 5340-5341
- O'Neil, G.W.¹ Phillips, A.²

16
- 61449150411
- and references cited therein
- I. Paterson N. M. Gardner G. J. Naylor Pure Appl. Chem. 2009 81 169 180
- (2009) Pure Appl. Chem. , vol.81 , pp. 169-180
- Paterson, I.¹ Gardner, N.M.² Naylor, G.J.³

17
- 62149085931
- See reference 9 and the following: I. Paterson N. M. Gardner E. Guzman A. E. Wright Bioorg. Med. Chem. 2009 17 2282 2289
- (2009) Bioorg. Med. Chem. , vol.17 , pp. 2282-2289
- Paterson, I.¹ Gardner, N.M.² Guzman, E.³ Wright, A.E.⁴

18
- 56249090051
- J. L. Eiseman L. Bai W.-H. Jung G. Moura-Letts B. W. Day D. P. Curran J. Med. Chem. 2008 51 6650 6653
- (2008) J. Med. Chem. , vol.51 , pp. 6650-6653
- Eiseman, J.L.¹ Bai, L.² Jung, W.-H.³ Moura-Letts, G.⁴ Day, B.W.⁵ Curran, D.P.⁶

19
- 34347251970
- W.-H. Jung C. Harrison Y. Shin J.-H. Fournier R. Balachandran B. S. Raccor R. P. Sikorski A. Vogt D. P. Curran B. W. Day J. Med. Chem. 2007 50 2951 2966
- (2007) J. Med. Chem. , vol.50 , pp. 2951-2966
- Jung, W.-H.¹ Harrison, C.² Shin, Y.³ Fournier, J.-H.⁴ Balachandran, R.⁵ Raccor, B.S.⁶ Sikorski, R.P.⁷ Vogt, A.⁸ Curran, D.P.⁹ Day, B.W.¹⁰

20
- 31544450706
- Y. Fukui A. M. Bruckner Y. Shin R. Balachandran B. W. Day D. P. Curran Org. Lett. 2006 8 301 304
- (2006) Org. Lett. , vol.8 , pp. 301-304
- Fukui, Y.¹ Bruckner, A.M.² Shin, Y.³ Balachandran, R.⁴ Day, B.W.⁵ Curran, D.P.⁶

21
- 77950287955
- J. S. Yadav V. Rajender Eur. J. Org. Chem. 2010 2148 2156
- (2010) Eur. J. Org. Chem. , pp. 2148-2156
- Yadav, J.S.¹ Rajender, V.²

22
- 67649311609
- H. L. Shimp G. C. Micalizio Tetrahedron 2009 65 5908 5915
- (2009) Tetrahedron , vol.65 , pp. 5908-5915
- Shimp, H.L.¹ Micalizio, G.C.²

23
- 64149114032
- L. C. Dias D. J. P. Lima C. C. S. Goncalves A. D. Andricopulo Eur. J. Org. Chem. 2009 1491 1494
- (2009) Eur. J. Org. Chem. , pp. 1491-1494
- Dias, L.C.¹ Lima, D.J.P.² Goncalves, C.C.S.³ Andricopulo, A.D.⁴

24
- 64349095239
- P. V. Ramachandran D. Pratihar Org. Lett. 2009 11 1467 1470
- (2009) Org. Lett. , vol.11 , pp. 1467-1470
- Ramachandran, P.V.¹ Pratihar, D.²

25
- 48549094863
- Ch. Zanato L. Pignataro Z. Hao C. Gennari Synthesis 2008 2158 2162
- (2008) Synthesis , pp. 2158-2162
- Zanato, Ch.¹ Pignataro, L.² Hao, Z.³ Gennari, C.⁴

26
- 37549005610
- A. K. Dilger V. Gopalsamuthiram S. D. Burke J. Am. Chem. Soc. 2007 129 16273 16277
- (2007) J. Am. Chem. Soc. , vol.129 , pp. 16273-16277
- Dilger, A.K.¹ Gopalsamuthiram, V.² Burke, S.D.³

27
- 34948891512
- V. Saibaba A. Sampath K. Mukkanti J. Iqbal P. Das Synthesis 2007 2797 2802
- (2007) Synthesis , pp. 2797-2802
- Saibaba, V.¹ Sampath, A.² Mukkanti, K.³ Iqbal, J.⁴ Das, P.⁵

28
- 35349026314
- Ch. Monti O. Sharon C. Gennari Chem. Commun. 2007 4271 4273
- (2007) Chem. Commun. , pp. 4271-4273
- Monti, Ch.¹ Sharon, O.² Gennari, C.³

29
- 34248668150
- O. Sharon Ch. Monti C. Gennari Tetrahedron 2007 63 5873 5878
- (2007) Tetrahedron , vol.63 , pp. 5873-5878
- Sharon, O.¹ Monti, Ch.² Gennari, C.³

30
- 33846404505
- G. Moura-Letts D. P. Curran Org. Lett. 2007 9 5 8
- (2007) Org. Lett. , vol.9 , pp. 5-8
- Moura-Letts, G.¹ Curran, D.P.²

31
- 79251500843
- J. Jaegel M. E. Maier Synlett 2006 693 696
- (2006) Synlett , pp. 693-696
- Jaegel, J.¹ Maier, M.E.²

32
- 33646440862
- Review:
- E. Prusov H. Roehm M. E. Maier Org. Lett. 2006 8 1025 1028
- (2006) Org. Lett. , vol.8 , pp. 1025-1028
- Prusov, E.¹ Roehm, H.² Maier, M.E.³

33
- 70349924940
- Recent references:
- M. C. Carreño G. Hernández-Torres M. Ribagorda A. Urbano Chem. Commun. 2009 6129 6144
- (2009) Chem. Commun. , pp. 6129-6144
- Carreño, M.C.¹ Hernández-Torres, G.² Ribagorda, M.³ Urbano, A.⁴

34
- 75749095138
- M. Lecea G. Hernández-Torres A. Urbano M. C. Carreño F. Colobert Org. Lett. 2010 12 580 583
- (2010) Org. Lett. , vol.12 , pp. 580-583
- Lecea, M.¹ Hernández-Torres, G.² Urbano, A.³ Carreño, M.C.⁴ Colobert, F.⁵

35
- 74049110556
- M. Barbarotto J. Geist S. Choppin F. Colobert Tetrahedron: Asymmetry 2009 20 2780 2787
- (2009) Tetrahedron: Asymmetry , vol.20 , pp. 2780-2787
- Barbarotto, M.¹ Geist, J.² Choppin, S.³ Colobert, F.⁴

36
- 70350665975
- A. Latorre A. Urbano M. C. Carreño Chem. Commun. 2009 6652 6654
- (2009) Chem. Commun. , pp. 6652-6654
- Latorre, A.¹ Urbano, A.² Carreño, M.C.³

37
- 70749103009
- F. Colobert V. Valdivia S. Choppin F. Leroux I. Fernández E. Álvarez N. Khiar Org. Lett. 2009 11 5130 5133
- (2009) Org. Lett. , vol.11 , pp. 5130-5133
- Colobert, F.¹ Valdivia, V.² Choppin, S.³ Leroux, F.⁴ Fernández, I.⁵ Álvarez, E.⁶ Khiar, N.⁷

38
- 70350623198
- G. Hernández-Torres A. Urbano M. C. Carreño F. Colobert Org. Lett. 2009 11 4930 4933
- (2009) Org. Lett. , vol.11 , pp. 4930-4933
- Hernández-Torres, G.¹ Urbano, A.² Carreño, M.C.³ Colobert, F.⁴

39
- 68949142763
- M. Obringer M. Barbarotto S. Choppin F. Colobert Org. Lett. 2009 11 3542 3545
- (2009) Org. Lett. , vol.11 , pp. 3542-3545
- Obringer, M.¹ Barbarotto, M.² Choppin, S.³ Colobert, F.⁴

40
- 0141563506
- M. Obringer F. Colobert B. Neugnot G. Solladié Org. Lett. 2003 5 629 632
- (2003) Org. Lett. , vol.5 , pp. 629-632
- Obringer, M.¹ Colobert, F.² Neugnot, B.³ Solladié, G.⁴

41
- 35948971134
- M. Obringer F. Colobert G. Solladié Eur. J. Org. Chem. 2006 1455 1467
- (2006) Eur. J. Org. Chem. , pp. 1455-1467
- Obringer, M.¹ Colobert, F.² Solladié, G.³

42
- 35948956235
- F. Colobert S. Choppin L. Ferreiro-Mederos M. Obringer S. Luengo-Arratta A. Urbano M. C. Carreño Org. Lett. 2007 9 4451 4454
- (2007) Org. Lett. , vol.9 , pp. 4451-4454
- Colobert, F.¹ Choppin, S.² Ferreiro-Mederos, L.³ Obringer, M.⁴ Luengo-Arratta, S.⁵ Urbano, A.⁶ Carreño, M.C.⁷

43
- 0002542424
- N. Kunieda J. Nokami M. Kinoshita Chem. Lett. 1974 369 372
- (1974) Chem. Lett. , pp. 369-372
- Kunieda, N.¹ Nokami, J.² Kinoshita, M.³

44
- 37049096419
- R. Annunziata M. Cinquini F. Cozzi J. Chem. Soc., Perkin Trans. 1 1979 1687 1690
- (1979) J. Chem. Soc., Perkin Trans. 1 , pp. 1687-1690
- Annunziata, R.¹ Cinquini, M.² Cozzi, F.³

45
- 0001296747
- M. C. Carreño J. L. García Ruano A. M. Martín C. Pedregal J. H. Rodríguez A. Rubio J. Sánchez J. Org. Chem. 1990 55 2120 2128
- (1990) J. Org. Chem. , vol.55 , pp. 2120-2128
- Carreño, M.C.¹ García Ruano, J.L.² Martín, A.M.³ Pedregal, C.⁴ Rodríguez, J.H.⁵ Rubio, A.⁶ Sánchez, J.⁷

46
- 35048884950
- Aldehyde (S)-7 was obtained from commercially available (S) Roche ester in 3 steps and 85% overall yield (see ESI) Determined by proton NMR analysis of the product. The minor component (12%) was a mixture of at least two diastereomers but we could not integrate the doublets corresponding to the methyl groups due to overlapping
- S. Akai Y. Kita Topics in Current Chemistry 2007 274 35 76
- (2007) Topics in Current Chemistry , vol.274 , pp. 35-76
- Akai, S.¹ Kita, Y.²

47
- 0001951357
- S. D. Rychnovsky B. N. Rogers T. I. Richardson Acc. Chem. Res. 1998 31 9 17
- (1998) Acc. Chem. Res. , vol.31 , pp. 9-17
- Rychnovsky, S.D.¹ Rogers, B.N.² Richardson, T.I.³

48
- 0025058974
- S. D. Rychnovsky D. J. Skalitzky Tetrahedron Lett. 1990 31 945 948
- (1990) Tetrahedron Lett. , vol.31 , pp. 945-948
- Rychnovsky, S.D.¹ Skalitzky, D.J.²

49
- 0025608552
- The correct structure of compound 13 was deduced from COSY, HMQC and HMBC NMR spectra (see ESI)
- D. A. Evans D. L. Rieger J. R. Gage Tetrahedron Lett. 1990 31 7099 7100
- (1990) Tetrahedron Lett. , vol.31 , pp. 7099-7100
- Evans, D.A.¹ Rieger, D.L.² Gage, J.R.³

50
- 63849216637
- Ch. Aissa European Journal of Organic Chemistry 2009 2009 1831 1844
- (2009) European Journal of Organic Chemistry , vol.2009 , pp. 1831-1844
- Aissa, Ch.¹

51
- 33646164915
- M. T. Crimmins A. C. DeBaillie J. Am. Chem. Soc. 2006 128 4936 4937
- (2006) J. Am. Chem. Soc. , vol.128 , pp. 4936-4937
- Crimmins, M.T.¹ Debaillie, A.C.²

52
- 11844282737
- I. Paterson O. Delgado G. J. Florence I. Lyothier M. O'Brien J. P. Scott N. Sereinig J. Org. Chem. 2005 70 150 160
- (2005) J. Org. Chem. , vol.70 , pp. 150-160
- Paterson, I.¹ Delgado, O.² Florence, G.J.³ Lyothier, I.⁴ O'Brien, M.⁵ Scott, J.P.⁶ Sereinig, N.⁷

53
- 0000693499
- I. Paterson A. Schlapbach Synlett 1995 498 500
- (1995) Synlett , pp. 498-500
- Paterson, I.¹ Schlapbach, A.²

54
- 0026607521
- P. Cintas Synthesis 1992 248 257
- (1992) Synthesis , pp. 248-257
- Cintas, P.¹

55
- 0036251475
- L. F. van Staden D. Gravestock D. J. Ager Chem. Soc. Rev. 2002 31 195 200
- (2002) Chem. Soc. Rev. , vol.31 , pp. 195-200
- Van Staden, L.F.¹ Gravestock, D.² Ager, D.J.³

56
- 0001008307
- C. H. Heathcock S. D. Young J. P. Hagen P. Pilli U. Badertscherad J. Org. Chem. 1985 50 2095 2105
- (1985) J. Org. Chem. , vol.50 , pp. 2095-2105
- Heathcock, C.H.¹ Young, S.D.² Hagen, J.P.³ Pilli, P.⁴ Badertscherad, U.⁵

57
- 0000710827
- J. S. Hubbard T. M. Harris J. Org. Chem. 1981 46 2566 2570
- (1981) J. Org. Chem. , vol.46 , pp. 2566-2570
- Hubbard, J.S.¹ Harris, T.M.²

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.