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Synlett

Volumn , Issue 14, 2007, Pages 2267-2271

Practical preparation of diosphenols by ring opening of α,β-epoxyketones catalyzed by silica gel supported acids

(6) Zhu, Rui a Xing, Lixin a Wang, Xinyan a Cheng, Chuanjie a Liu, Bo a Hu, Yuefei a

a Tsinghua University (China)

Author keywords

Green chemistry; Peroxides; Regioselective; Ring opening; Supported catalysis

Indexed keywords

ALPHA BETA EPOXYKETONE; DIOSPHENOL DERIVATIVE; KETONE DERIVATIVE; PHENOL DERIVATIVE; SILICA GEL; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; RING OPENING; SYNTHESIS;

EID: 34548727332 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-985584 Document Type: Article

Times cited : (14)

References (51)

1
- 0037434546
- For selected references, see: a
- For selected references, see: (a) Murakami, N.; Sugimoto, M.; Kawanishi, M.; Tamura, S.; Kim, H.-S.; Begum, K.; Wataya, Y.; Kobayashi, M. J. Med. Chem. 2003, 46, 638.
- (2003) J. Med. Chem , vol.46 , pp. 638
- Murakami, N.¹ Sugimoto, M.² Kawanishi, M.³ Tamura, S.⁴ Kim, H.-S.⁵ Begum, K.⁶ Wataya, Y.⁷ Kobayashi, M.⁸

2
- 0038645112
- (b) Li, A.; She, X.; Zhang, J.; Wu, T.; Pan, X. Tetrahedron 2003, 59, 5737.
- (2003) Tetrahedron , vol.59 , pp. 5737
- Li, A.¹ She, X.² Zhang, J.³ Wu, T.⁴ Pan, X.⁵

3
- 0037040680
- (c) Pena-Cabrera, E.; Liebeskind, L. S. J. Org. Chem. 2002, 67, 1689.
- (2002) J. Org. Chem , vol.67 , pp. 1689
- Pena-Cabrera, E.¹ Liebeskind, L.S.²

4
- 0035188733
- (d) Ottinger, H.; Soldo, T.; Hofmann, T. J. Agric Food Chem. 2001, 49, 5383.
- (2001) J. Agric Food Chem , vol.49 , pp. 5383
- Ottinger, H.¹ Soldo, T.² Hofmann, T.³

5
- 0032555395
- (e) Yin, J.; Liebeskind, L. S. J. Org. Chem. 1998, 63, 5726.
- (1998) J. Org. Chem , vol.63 , pp. 5726
- Yin, J.¹ Liebeskind, L.S.²

6
- 0027181893
- (f) Decosterd, L. A.; Ian, C. P.; Gustafson, K. R.; Cardellina, J. H.; McMahon, J. B. II; Cragg, G. M.; Murata, Y.; Pannell, L. K.; Steiner, J. R.; Clardy, J.; Boyd, M. R. J. Am. Chem. Soc. 1993, 115, 6673.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 6673
- Decosterd, L.A.¹ Ian, C.P.² Gustafson, K.R.³ Cardellina, J.H.⁴ McMahon II, J.B.⁵ Cragg, G.M.⁶ Murata, Y.⁷ Pannell, L.K.⁸ Steiner, J.R.⁹ Clardy, J.¹⁰ Boyd, M.R.¹¹

7
- 0025190551
- (g) Sasaki, M.; Murae, T.; Takahashi, T. J. Org. Chem. 1990, 55, 528.
- (1990) J. Org. Chem , vol.55 , pp. 528
- Sasaki, M.¹ Murae, T.² Takahashi, T.³

8
- 0015921169
- (h) Kupchan, S. M.; Britton, R. W.; Sigel, C. W. J. Org. Chem. 1973, 38, 178.
- (1973) J. Org. Chem , vol.38 , pp. 178
- Kupchan, S.M.¹ Britton, R.W.² Sigel, C.W.³

9
- 26444502089
- For selected references, see: a
- For selected references, see: (a) Cepa, M. M. D. S.; Tavares da Silva, E. J.; Correia-da-Silva, G.; Roleira, F. M. F.; Teixeira, N. A. A. J. Med. Chem. 2005, 48, 6379.
- (2005) J. Med. Chem , vol.48 , pp. 6379
- Cepa, M.M.D.S.¹ Tavares da Silva, E.J.² Correia-da-Silva, G.³ Roleira, F.M.F.⁴ Teixeira, N.A.A.⁵

10
- 2942663398
- (b) Solorio, C. R.; Rodriguez-Cendejas, C. G.; Pena-Cabrera, E. ARKIVOC 2003, (xi), 172.
- (2003) ARKIVOC , vol.11 , pp. 172
- Solorio, C.R.¹ Rodriguez-Cendejas, C.G.² Pena-Cabrera, E.³

11
- 0035415403
- (c) Ciobanu, L. C.; Boivin, R. P.; Luu-The, V.; Poirier, D. Eur. J. Med. Chem. 2001, 36, 659.
- (2001) Eur. J. Med. Chem , vol.36 , pp. 659
- Ciobanu, L.C.¹ Boivin, R.P.² Luu-The, V.³ Poirier, D.⁴

12
- 0028958197
- (d) Li, X.; Singh, S. M.; Cote, J.; Laplante, S.; Veilleux, R.; Labrie, F. J. Med. Chem. 1995, 38, 1456.
- (1995) J. Med. Chem , vol.38 , pp. 1456
- Li, X.¹ Singh, S.M.² Cote, J.³ Laplante, S.⁴ Veilleux, R.⁵ Labrie, F.⁶

13
- 34548717613
- (e) Brodie, A. M. J. Steroid Biochem. Mol. Biol. 1994, 28, 788.
- (1994) Steroid Biochem. Mol. Biol , vol.28 , pp. 788
- Brodie, A.M.J.¹

14
- 33646799124
- For selected references, see: a
- For selected references, see: (a) Paju, A.; Laos, M.; Jogi, A.; Paeri, M.; Jaeaelaid, R.; Pehk, T.; Kanger, T.; Lopp, M. Tetrahedron Lett. 2006, 47, 4491.
- (2006) Tetrahedron Lett , vol.47 , pp. 4491
- Paju, A.¹ Laos, M.² Jogi, A.³ Paeri, M.⁴ Jaeaelaid, R.⁵ Pehk, T.⁶ Kanger, T.⁷ Lopp, M.⁸

15
- 33646455000
- (b) Wu, J.; Li, H.; Sun, L.; Dai, W.-M. Tetrahedron 2006, 62, 4643.
- (2006) Tetrahedron , vol.62 , pp. 4643
- Wu, J.¹ Li, H.² Sun, L.³ Dai, W.-M.⁴

16
- 20344370975
- (c) Svennebring, A.; Garg, N.; Nilsson, P.; Hallberg, A.; Larhed, M. J. Org. Chem. 2005, 70, 4720.
- (2005) J. Org. Chem , vol.70 , pp. 4720
- Svennebring, A.¹ Garg, N.² Nilsson, P.³ Hallberg, A.⁴ Larhed, M.⁵

17
- 34548797087
- (d) Loebel, J.; Herdtweck, E.; Bach, T. Eur. J. Org. Chem. 2003, 4146.
- (2003) Eur. J. Org. Chem , pp. 4146
- Loebel, J.¹ Herdtweck, E.² Bach, T.³

18
- 0037454658
- (e) Martinez, R.; Jimenez-Vazquez, H. A.; Delgado, F.; Tamariz, J. Tetrahedron 2003, 59, 481.
- (2003) Tetrahedron , vol.59 , pp. 481
- Martinez, R.¹ Jimenez-Vazquez, H.A.² Delgado, F.³ Tamariz, J.⁴

19
- 0034685525
- (f) Trost, B. M.; Schroeder, G. M. J. Am. Chem. Soc. 2000, 122, 3785.
- (2000) J. Am. Chem. Soc , vol.122 , pp. 3785
- Trost, B.M.¹ Schroeder, G.M.²

20
- 0001136970
- (g) Utaka, M.; Kuriki, H.; Sakai, T.; Takeda, A. J. Org. Chem. 1986, 51, 935.
- (1986) J. Org. Chem , vol.51 , pp. 935
- Utaka, M.¹ Kuriki, H.² Sakai, T.³ Takeda, A.⁴

21
- 0001689251
- (h) Koreeda, M.; Luengo, J. I. J. Am. Chem. Soc. 1985, 107, 5572.
- (1985) J. Am. Chem. Soc , vol.107 , pp. 5572
- Koreeda, M.¹ Luengo, J.I.²

22
- 0000050843
- (i) Ponaras, A. A. J. Org. Chem. 1983, 48, 3866.
- (1983) J. Org. Chem , vol.48 , pp. 3866
- Ponaras, A.A.¹

23
- 0012354633
- (j) Dauben, W. G.; Ponaras, A. A.; Chollet, A. J. Org. Chem. 1980, 45, 4413.
- (1980) J. Org. Chem , vol.45 , pp. 4413
- Dauben, W.G.¹ Ponaras, A.A.² Chollet, A.³

24
- 0035133188
- (a) de Frutos, O.; Atienza, C.; Echavarren, A. M. Eur. J. Org. Chem. 2001, 163.
- (2001) Eur. J. Org. Chem , pp. 163
- de Frutos, O.¹ Atienza, C.² Echavarren, A.M.³

25
- 0034684495
- (b) Ponaras, A. A.; Meah, M. Y. Tetrahedron Lett. 2000, 41, 9031.
- (2000) Tetrahedron Lett , vol.41 , pp. 9031
- Ponaras, A.A.¹ Meah, M.Y.²

26
- 0027189896
- (c) Paquette, L. A.; Wang, T. Z.; Vo, N. H. J. Am. Chem. Soc. 1993, 115, 1676.
- (1993) J. Am. Chem. Soc , vol.115 , pp. 1676
- Paquette, L.A.¹ Wang, T.Z.² Vo, N.H.³

27
- 0027207528
- (d) Nagasawa, K.; Matauda, N.; Noguchi, Y.; Yamanashi, M.; Zako, Y.; Shimizu, I. J. Org. Chem. 1993, 58, 1483.
- (1993) J. Org. Chem , vol.58 , pp. 1483
- Nagasawa, K.¹ Matauda, N.² Noguchi, Y.³ Yamanashi, M.⁴ Zako, Y.⁵ Shimizu, I.⁶

28
- 0005737652
- (e) Becker, D.; Birnbaum, D. J. Org. Chem. 1980, 45, 570.
- (1980) J. Org. Chem , vol.45 , pp. 570
- Becker, D.¹ Birnbaum, D.²

29
- 0031116495
- (a) Harrity, J. P. A.; Kerr, W. J.; Middlemiss, D.; Scott, J. S. J. Organomet. Chem. 1997, 532, 219.
- (1997) J. Organomet. Chem , vol.532 , pp. 219
- Harrity, J.P.A.¹ Kerr, W.J.² Middlemiss, D.³ Scott, J.S.⁴

30
- 0343283589
- (b) Verma, A. K.; Gupta, R.; Yadav, M. R.; Sharma, N.; Jindal, D. P. Indian J. Chem., Sect. B 1995, 34, 215.
- (1995) Indian J. Chem., Sect. B , vol.34 , pp. 215
- Verma, A.K.¹ Gupta, R.² Yadav, M.R.³ Sharma, N.⁴ Jindal, D.P.⁵

31
- 37049068820
- (c) Haase-Held, M.; Hatzis, J. M. J. Chem. Soc., Perkin Trans. 1 1993, 2907.
- (1993) J. Chem. Soc., Perkin Trans. 1 , pp. 2907
- Haase-Held, M.¹ Hatzis, J.M.²

32
- 0026656474
- (d) Lesuisse, D.; Gourvest, J. F.; Hartmann, C.; Benslimane, T. O.; Philibert, D.; Vevert, J. P. J. Med. Chem. 1992, 35, 1588.
- (1992) J. Med. Chem , vol.35 , pp. 1588
- Lesuisse, D.¹ Gourvest, J.F.² Hartmann, C.³ Benslimane, T.O.⁴ Philibert, D.⁵ Vevert, J.P.⁶

33
- 0026656474
- (e) Lesuisse, D.; Gourvest, J. F.; Hartmann, C.; Benslimane, T. O.; Philibert, D.; Vevert, J. P. J. Med. Chem. 1992, 35, 1588.
- (1992) J. Med. Chem , vol.35 , pp. 1588
- Lesuisse, D.¹ Gourvest, J.F.² Hartmann, C.³ Benslimane, T.O.⁴ Philibert, D.⁵ Vevert, J.P.⁶

34
- 3343020345
- (f) Mastalerz, H.; Morand, P. J. Org. Chem. 1981, 46, 1206.
- (1981) J. Org. Chem , vol.46 , pp. 1206
- Mastalerz, H.¹ Morand, P.²

35
- 0018198974
- (g) Jennings, B. H.; Bengtson, J. M. Steroids 1978, 31, 49.
- (1978) Steroids , vol.31 , pp. 49
- Jennings, B.H.¹ Bengtson, J.M.²

36
- 0036173409
- (a) Tavares da Silva, E. J.; Roleira, F. M. F.; Sae Melo, M. L.; Campos Neves, A. S.; Paixao, J. A.; de Almeida, M. J.; Silva, M. R.; Andrade, L. C. R. Steroids 2002, 67, 311.
- (2002) Steroids , vol.67 , pp. 311
- Tavares da Silva, E.J.¹ Roleira, F.M.F.² Sae Melo, M.L.³ Campos Neves, A.S.⁴ Paixao, J.A.⁵ de Almeida, M.J.⁶ Silva, M.R.⁷ Andrade, L.C.R.⁸

37
- 0011165604
- (b) Constantino, M. G.; Lacerda, J. V.; Aragao, V. Molecular 2001, 6, 770.
- (2001) Molecular , vol.6 , pp. 770
- Constantino, M.G.¹ Lacerda, J.V.² Aragao, V.³

38
- 0000398414
- (c) Sankararaman, S.; Nesakumar, J. J. Chem. Soc., Perkin Trans. 1 1999, 3173.
- (1999) J. Chem. Soc., Perkin Trans. 1 , pp. 3173
- Sankararaman, S.¹ Nesakumar, J.²

39
- 0033105263
- (d) Campos Neves, A. S.; Sáe Melo, M. L.; Moreno, M. J. S. M.; Tavares da Silva, E. J.; Salvado, J. A. R.; da Costa, S. P.; Martins, R. M. L. M. Tetrahedron 1999, 55, 3255.
- (1999) Tetrahedron , vol.55 , pp. 3255
- Campos Neves, A.S.¹ Sáe Melo, M.L.² Moreno, M.J.S.M.³ Tavares da Silva, E.J.⁴ Salvado, J.A.R.⁵ da Costa, S.P.⁶ Martins, R.M.L.M.⁷

40
- 0024586858
- (e) Bednarski, P. J.; Nelson, S. D. J. Med. Chem. 1989, 32, 203.
- (1989) J. Med. Chem , vol.32 , pp. 203
- Bednarski, P.J.¹ Nelson, S.D.²

41
- 33845281348
- (f) Klix, R. C.; Bach, R. D. J. Org. Chem. 1987, 52, 580.
- (1987) J. Org. Chem , vol.52 , pp. 580
- Klix, R.C.¹ Bach, R.D.²

42
- 0021915174
- (g) Schultz, A. G.; Lucci, R. D.; Napier, J. J.; Kinoshita, H.; Ravichandran, R.; Shannon, P.; Yee, Y. K. J. Org. Chem. 1985, 50, 217.
- (1985) J. Org. Chem , vol.50 , pp. 217
- Schultz, A.G.¹ Lucci, R.D.² Napier, J.J.³ Kinoshita, H.⁴ Ravichandran, R.⁵ Shannon, P.⁶ Yee, Y.K.⁷

43
- 84926526160
- Sleman, S.; Eartham, J. F. Quart. Rev. 1960, 14, 221.
- (1960) Quart. Rev , vol.14 , pp. 221
- Sleman, S.¹ Eartham, J.F.²

44
- 0007177773
- (a) Reusch, W. R.; LeMahieu, R. J. Org. Chem. 1963, 28, 2443.
- (1963) J. Org. Chem , vol.28 , pp. 2443
- Reusch, W.R.¹ LeMahieu, R.²

45
- 0024449011
- (b) Kawada, K.; Kim, M.; Watt, D. S. Tetrahedron Lett. 1989, 30, 5985.
- (1989) Tetrahedron Lett , vol.30 , pp. 5985
- Kawada, K.¹ Kim, M.² Watt, D.S.³

46
- 34247564607
- (a) Cao, L.; Sun, J.; Wang, X.; Zhu, R.; Shi, H.; Hu, Y. Tetrahedron 2007, 63, 5036.
- (2007) Tetrahedron , vol.63 , pp. 5036
- Cao, L.¹ Sun, J.² Wang, X.³ Zhu, R.⁴ Shi, H.⁵ Hu, Y.⁶

47
- 33749234158
- (b) Wang, C.; Rath, N. P.; Covey, D. F. Tetrahedron Lett. 2006, 47, 7837.
- (2006) Tetrahedron Lett , vol.47 , pp. 7837
- Wang, C.¹ Rath, N.P.² Covey, D.F.³

48
- 0037764711
- (c) Wang, C.; Jiang, X.; Shi, H.; Lu, J.; Hu, Y.; Hu, H. J. Org. Chem. 2003, 68, 4579.
- (2003) J. Org. Chem , vol.68 , pp. 4579
- Wang, C.¹ Jiang, X.² Shi, H.³ Lu, J.⁴ Hu, Y.⁵ Hu, H.⁶

49
- 0034596040
- (d) Jiang, X.; Wang, C.; Hu, Y.; Hu, H.; Covey, D. F. J. Org. Chem. 2000, 65, 3555.
- (2000) Org. Chem , vol.65 , pp. 3555
- Jiang, X.¹ Wang, C.² Hu, Y.³ Hu, H.⁴ Covey, D.F.J.⁵

50
- 0034042761
- Elings, J. A.; Lempers, H. B.; Sheldon, R. A. Eur. J. Org. Chem. 2000, 1905.
- (2000) Eur. J. Org. Chem , pp. 1905
- Elings, J.A.¹ Lempers, H.B.² Sheldon, R.A.³

51
- 34548776977
- Typical Procedure for the Preparation of 3d: The mixture of substrate 4d (1.0 g, the mixed acid [2.0 mL, H2SO 4-HOAc (1:2 wt/wt, and silica gel (8.0 g) in THF (10 mL) was rotaevaporated in vacuum (<15 mmHg) at 70°C. After the solvent had been removed, the reaction was continued for another 3 min. The resultant non-stick solid was then washed with CH2Cl2 and the combined organic layers were washed with aq Na2CO3, brine and dried over Na2SO4. Removal of the solvent yielded the crude product, which was purified by chromatography to give the pure product 3d (0.81 g, 81%)as white crystals; mp 88-90°C (EtOAc-PE, α]D 20 +277.86° (c, 1.20, CHCl3, IR: 3386, 2958, 2937, 2871, 1739, 1661 cm-1. 1H NMR: δ, 6.17 (s, 1 H, 3.02-3.06 (m, 1 H, 2.61-2.75 (m, 4 H, 2.39-2.46 (m, 1 H, 2.07-2.09 m, 1 H
- 13C NMR spectra are available upon request from the authors.

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