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Synlett

Volumn , Issue 6, 2007, Pages 989-991

A practical approach to stereochemically defined tetrahydrofurans from [5+2] oxidopyrylium-alkene cycloadducts

(4) Yadav, Arun A a Sarang, Prajakta S a Trivedi, Girish K a Salunkhe, Manikrao M a

a INSTITUTE OF SCIENCE (India)

Author keywords

Beckmann fission; Cleavage; Cycloaddition; Oxidopyrylium; Stereoselectivity

Indexed keywords

3 OXIDOPYRYLIUM BETAINE; ALKENE DERIVATIVE; BETAINE; TETRAHYDROFURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BECKMANN REARRANGEMENT; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CYCLOADDITION; STEREOCHEMISTRY;

EID: 34247167568 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-973866 Document Type: Article

Times cited : (8)

References (43)

1
- 0027200955
- (a) Harmange, J. C.; Figadere, B. Tetrahedron: Asymmetry 1993, 4, 1711.
- (1993) Tetrahedron: Asymmetry , vol.4 , pp. 1711
- Harmange, J.C.¹ Figadere, B.²

2
- 15844366864
- (b) Bovin, T. L. B. Tetrahedron 1987, 43, 3309.
- (1987) Tetrahedron , vol.43 , pp. 3309
- Bovin, T.L.B.¹

3
- 49149146087
- (c) Bartlett, P. A. Tetrahedron 1980, 36, 2.
- (1980) Tetrahedron , vol.36 , pp. 2
- Bartlett, P.A.¹

4
- 0000012312
- Academic Press: Florida, Chap. 6
- (d) Bartlett, P. A. Asymmetric Synthesis, Vol. III; Academic Press: Florida, 1984, Chap. 6, 411.
- (1984) Asymmetric Synthesis , vol.3 , pp. 411
- Bartlett, P.A.¹

5
- 0000178470
- (e) Semple, J. E.; Jouillie, M. Heterocycles 1980, 14, 1825.
- (1980) Heterocycles , vol.14 , pp. 1825
- Semple, J.E.¹ Jouillie, M.²

6
- 0030752370
- (a) Koert, U.; Stein, M.; Wagner, H. Chem. Eur. J. 1997, 3, 1170.
- (1997) Chem. Eur. J , vol.3 , pp. 1170
- Koert, U.¹ Stein, M.² Wagner, H.³

7
- 0029592717
- (b) Hoppe, R.; Scharf, H. D. Synthesis 1995, 1447.
- (1995) Synthesis , pp. 1447
- Hoppe, R.¹ Scharf, H.D.²

8
- 0000964586
- For representative recent examples of tetrahydrofuran syntheses, see: a, Bird, C. W, Ed, Pergamon Press: Oxford
- For representative recent examples of tetrahydrofuran syntheses, see: (a) Friedrichsen, W. In Comprehensive Heterocyclic Chemistry II, Vol. 2; Bird, C. W., Ed.; Pergamon Press: Oxford, 1996, 351.
- (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 351
- Friedrichsen, W.¹

9
- 0000020825
- (b) Eames, J.; Jones, R. V. H.; Warren, S. Tetrahedron Lett. 1996, 37, 4823.
- (1996) Tetrahedron Lett , vol.37 , pp. 4823
- Eames, J.¹ Jones, R.V.H.² Warren, S.³

10
- 0031584879
- (c) Andrey, O.; Glanzmann, C.; Landais, Y.; Parra, R. L. Tetrahedron 1997, 53, 2835.
- (1997) Tetrahedron , vol.53 , pp. 2835
- Andrey, O.¹ Glanzmann, C.² Landais, Y.³ Parra, R.L.⁴

11
- 0034740834
- (d) Elliott, M. C.; Williams, E. J. Chem. Soc., Perkin Trans. 1 2001, 2303.
- (2001) J. Chem. Soc., Perkin Trans. 1 , pp. 2303
- Elliott, M.C.¹ Williams, E.²

12
- 0000697605
- (e) Mascarenas, J. L.; Rumbo, A.; Castedo, L. J. Org. Chem. 1997, 62, 8620.
- (1997) J. Org. Chem , vol.62 , pp. 8620
- Mascarenas, J.L.¹ Rumbo, A.² Castedo, L.³

13
- 13844253295
- and pertinent references therein
- (f) Fishwick, C. W. G.; Mitchell, G.; Pang, P. F. W. Synlett 2005, 285; and pertinent references therein.
- (2005) Synlett , pp. 285
- Fishwick, C.W.G.¹ Mitchell, G.² Pang, P.F.W.³

14
- 0003523008
- For review, see: a, Pergamon Press: New York
- For review, see: (a) Carruthers, W. Cycloaddition Reactions in Organic Synthesis; Pergamon Press: New York, 1990, .
- (1990) Cycloaddition Reactions in Organic Synthesis
- Carruthers, W.¹

15
- 0003905731
- Morrison, J. D, Ed, Academic Press: New York
- (b) Paquette, L. A. Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: New York, 1984.
- (1984) Asymmetric Synthesis
- Paquette, L.A.¹

16
- 0347380038
- (a) Murali Krishna, U.; Srikanth, G. S. C.; Trivedi, G. K.; Deodhar, K. D. Synlett 2003, 2383.
- (2003) Synlett , pp. 2383
- Murali Krishna, U.¹ Srikanth, G.S.C.² Trivedi, G.K.³ Deodhar, K.D.⁴

17
- 0842264095
- (b) Murali Krishna, U.; Deodhar, K. D.; Trivedi, G. K.; Shaikh, M. J. Org. Chem. 2004, 69, 967.
- (2004) J. Org. Chem , vol.69 , pp. 967
- Murali Krishna, U.¹ Deodhar, K.D.² Trivedi, G.K.³ Shaikh, M.⁴

18
- 0346996547
- (c) Murali Krishna, U.; Trivedi, G. K. Tetrahedron Lett. 2004, 45, 257.
- (2004) Tetrahedron Lett , vol.45 , pp. 257
- Murali Krishna, U.¹ Trivedi, G.K.²

19
- 2342586551
- (d) Murali Krishna, U.; Deodhar, K. D.; Trivedi, G. K. Tetrahedron 2004, 60, 4829.
- (2004) Tetrahedron , vol.60 , pp. 4829
- Murali Krishna, U.¹ Deodhar, K.D.² Trivedi, G.K.³

20
- 0038674937
- (a) Hendrickson, J. B.; Farina, J. S. J. Org. Chem. 1980, 45, 3361.
- (1980) J. Org. Chem , vol.45 , pp. 3361
- Hendrickson, J.B.¹ Farina, J.S.²

21
- 37049096409
- (b) Sammes, P. G.; Street, L. J. J. Chem. Soc., Chem. Commun. 1982, 1056.
- (1982) J. Chem. Soc., Chem. Commun , pp. 1056
- Sammes, P.G.¹ Street, L.J.²

22
- 37049099771
- (c) Sammes, P. G.; Street, L. J. J. Chem. Soc., Perkin Trans. 1 1983, 1261.
- (1983) J. Chem. Soc., Perkin Trans. 1 , pp. 1261
- Sammes, P.G.¹ Street, L.J.²

23
- 33947332002
- (a) Ohno, M.; Terasawa, I. J. Am. Chem. Soc. 1966, 88, 5683.
- (1966) J. Am. Chem. Soc , vol.88 , pp. 5683
- Ohno, M.¹ Terasawa, I.²

24
- 34247103421
- (b) Boaz, A.; Hassner, A. Synthesis 1978, 932.
- (1978) Synthesis , pp. 932
- Boaz, A.¹ Hassner, A.²

25
- 0029904975
- (c) Han, M.; Covey, D. F. J. Org. Chem. 1996, 61, 7614.
- (1996) Org. Chem , vol.61 , pp. 7614
- Han, M.¹ Covey, D.F.J.²

26
- 0034596040
- (d) Wang, K. J. C.; Hu, Y.; Hu, H.; Covey, D. F. J. Org. Chem. 2000, 65, 3555.
- (2000) J. Org. Chem , vol.65 , pp. 3555
- Wang, K.J.C.¹ Hu, Y.² Hu, H.³ Covey, D.F.⁴

27
- 0037169040
- (e) Rosenberg, M. G.; Haslinger, U.; Brinker, U. H. J. Org. Chem. 2002, 67, 450.
- (2002) J. Org. Chem , vol.67 , pp. 450
- Rosenberg, M.G.¹ Haslinger, U.² Brinker, U.H.³

28
- 2942544735
- (f) Iglesias-Arteaga, M. A.; Sandoval-Ramirez, J.; Mata-Esma, M. Y.; Vinas-Bravo, O.; Bernes, S. Tetrahedron Lett. 2004, 45, 4921.
- (2004) Tetrahedron Lett , vol.45 , pp. 4921
- Iglesias-Arteaga, M.A.¹ Sandoval-Ramirez, J.² Mata-Esma, M.Y.³ Vinas-Bravo, O.⁴ Bernes, S.⁵

29
- 29744448556
- (g) Blaszczyk, K.; Koenig, H.; Mel, K.; Paryzek, Z. Tetrahedron 2006, 62, 1069.
- (2006) Tetrahedron , vol.62 , pp. 1069
- Blaszczyk, K.¹ Koenig, H.² Mel, K.³ Paryzek, Z.⁴

30
- 0342975243
- (a) Petrier, C.; Luche, J. L. Tetrahedron Lett. 1987, 28, 2347.
- (1987) Tetrahedron Lett , vol.28 , pp. 2347
- Petrier, C.¹ Luche, J.L.²

31
- 0032567945
- (b) Alonso, F.; Yus, M. Tetrahedron 1998, 54, 1921.
- (1998) Tetrahedron , vol.54 , pp. 1921
- Alonso, F.¹ Yus, M.²

32
- 33746171646
- (c) Laval, G.; Holding, B. T. Synlett 2003, 279.
- (2003) Synlett , pp. 279
- Laval, G.¹ Holding, B.T.²

33
- 0001233144
- (d) Saito, S.; Yamamoto, H. J. Org. Chem. 1996, 61, 2928.
- (1996) J. Org. Chem , vol.61 , pp. 2928
- Saito, S.¹ Yamamoto, H.²

34
- 0028050121
- (e) Belisle, C. M.; Young, Y. M.; Singaram, B. Tetrahedron Lett. 1994, 35, 5595.
- (1994) Tetrahedron Lett , vol.35 , pp. 5595
- Belisle, C.M.¹ Young, Y.M.² Singaram, B.³

35
- 1842478923
- (a) Khurana, J. M.; Sharma, P. Bull. Chem. Soc. Jpn. 2004, 77, 549.
- (2004) Bull. Chem. Soc. Jpn , vol.77 , pp. 549
- Khurana, J.M.¹ Sharma, P.²

36
- 33845374200
- (b) Ganem, B.; Osby, J. O. Chem. Rev. 1986, 86, 763.
- (1986) Chem. Rev , vol.86 , pp. 763
- Ganem, B.¹ Osby, J.O.²

37
- 34247169772
- General procedure for the reduction of cycloadduct 5: To cycloadduct 5 (1 mmol) dissolved in MeOH (12 mL) was added NiCl 2·6H2O (5 mmol) followed by distilled H 2O (2 mL, NaBH4 (2 mmol) was then added and the reaction mixture was stirred vigorously at r.t, The progress of the reaction was monitored by TLC using PE-EtOAc (9:1) and showed the complete disappearance of starting material after 15 min. The reaction was quenched with MeOH (10 mL) and the reaction mixture was filtered through a pad of celite and washed with MeOH. H2O (50 mL) was added to the combined filtrate, which was extracted with CH2Cl2 (3 x 15 mL, The combined CH 2Cl2 extract was dried over anhyd MgSO4, decanted through a cotton pad and concentrated in vacuo. The product was purified by column chromatography using silica gel (60-120 mesh) and PE-EtOAc as eluent
- 4, decanted through a cotton pad and concentrated in vacuo. The product was purified by column chromatography using silica gel (60-120 mesh) and PE-EtOAc as eluent.

38
- 34247111098
- 4, decanted through a cotton pad and concentrated in vacuo. The product was purified by column chromatography using silica gel (60-120 mesh) and PE-EtOAc (9:1) as eluent.
- 4, decanted through a cotton pad and concentrated in vacuo. The product was purified by column chromatography using silica gel (60-120 mesh) and PE-EtOAc (9:1) as eluent.

39
- 34247138594
- Typical procedure: A slight excess of SOCl2 (1 g, 8.4 mmol) in anhyd CCl4 (15 mL) at 0°C was added over a few minutes to a solution of oxime 6 (R, OEt, 1.5 g, 8 mmol) in CCl4, also at 0°C. Immediately after the addition, vigorous evolution of H 2 took place, the mixture was allowed to stir for another 10 min and then MeOH (10 mL) was added and the resulting solution was stirred for another 30 min. The solution was quenched with NaHCO3 and extracted using CH2Cl2 (2 x 30 mL, Evaporation of the solvent in vacuo and column chromatography of the residue on silica gel (EtOAc-PE, 1:9) gave tetrahydrofuran 7 (R, OEt) as a pale yellow oil (1.7 g, 90, IR: 2922, 2243, 1107, 1045 cm-1; 1H NMR (500 MHz, CDCl3, δ, 5.02 (dd, J, 1.5, 3.3 Hz, 1 H, 4.10 (m, 1 H, 4.06 (m, 1 H) 3.55 (m, 1 H, 3.34 (s, 3 H, 3.33 (m, 1 H, 2.60-2.50 m, 2 H, 2.1
- 3Na: 222.1106; found: 222.1105.

40
- 33846003822
- and references cited therein
- (a) Ishiwata, A.; Akao, H.; Ito, Y. Org. Lett. 2006, 5525; and references cited therein,
- (2006) Org. Lett , pp. 5525
- Ishiwata, A.¹ Akao, H.² Ito, Y.³

41
- 0000989744
- (b) Vargeese, C.; Abushanab, C. J. Org. Chem. 1990, 55, 4400.
- (1990) J. Org. Chem , vol.55 , pp. 4400
- Vargeese, C.¹ Abushanab, C.²

42
- 0037423170
- (c) Sasmal, P. K.; Maier, M. E. J. Org. Chem. 2003, 68, 824.
- (2003) J. Org. Chem , vol.68 , pp. 824
- Sasmal, P.K.¹ Maier, M.E.²

43
- 33845238277
- (d) Wolfe, J. P.; Hay, M. B. Tetrahedron 2007, 63, 261.
- (2007) Tetrahedron , vol.63 , pp. 261
- Wolfe, J.P.¹ Hay, M.B.²

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