SCOPUS 정보 검색 플랫폼

Volumn , Issue 16, 2007, Pages 2590-2592

Synthesis of semicyclic dienes by modified Julia olefination of vinyl sulfones derived from carbohydrates

Author keywords

Aromatic aldehydes; Carbohydrate; Dienes; Modified Julia olefination; Vinyl sulfones

Indexed keywords

ALKADIENE; CARBOHYDRATE DERIVATIVE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG; VINYL SULFONE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; ELIMINATION REACTION; OLEFINATION; SYNTHESIS;

EID: 35348973084 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2007-986655 Document Type: Article

Times cited : (4)

References (23)

1
- 0003796479
- American Chemical Society: Washington, DC
- Giuliano, R. M. Cycloaddition Reactions in Carbohydrate Chemistry; American Chemical Society: Washington / DC, 1992.
- (1992) Cycloaddition Reactions in Carbohydrate Chemistry
- Giuliano, R.M.¹

2
- 0042295746
- (a) Sun, K. M.; Fraser-Reid, B.; Tam, T. F. J. Am. Chem. Soc. 1982, 104, 367.
- (1982) J. Am. Chem. Soc , vol.104 , pp. 367
- Sun, K.M.¹ Fraser-Reid, B.² Tam, T.F.³

3
- 0000032163
- (b) Sun, K. M.; Giuliano, R. M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 4774.
- (1985) J. Org. Chem , vol.50 , pp. 4774
- Sun, K.M.¹ Giuliano, R.M.² Fraser-Reid, B.³

4
- 0002440194
- (c) Giuliano, R. M.; Buzby, J. H. Carbohydr. Res. 1986, 158, C1.
- (1986) Carbohydr. Res , vol.158
- Giuliano, R.M.¹ Buzby, J.H.²

5
- 37049067093
- (d) Lopez, J. C.; Lameignere, E.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 706.
- (1988) J. Chem. Soc., Chem. Commun , pp. 706
- Lopez, J.C.¹ Lameignere, E.² Lukacs, G.³

6
- 1642412660
- (e) Lipshutz, B. H.; Nguyen, S. L.; Elworthy, T. R. Tetrahedron 1988, 44, 3355.
- (1988) Tetrahedron , vol.44 , pp. 3355
- Lipshutz, B.H.¹ Nguyen, S.L.² Elworthy, T.R.³

7
- 0025126483
- (f) Burnouf, C.; Lopez, J. C.; Calvo-Flores, F. G.; Laborde, M. A.; Olesker, A.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1990, 823.
- (1990) J. Chem. Soc., Chem. Commun , pp. 823
- Burnouf, C.¹ Lopez, J.C.² Calvo-Flores, F.G.³ Laborde, M.A.⁴ Olesker, A.⁵ Lukacs, G.⁶

8
- 0024997294
- (g) Giuliano, R. M.; Buzby, J. H.; Macropulos, N.; Springer, J. P. J. Org. Chem. 1990, 55, 3555.
- (1990) J. Org. Chem , vol.55 , pp. 3555
- Giuliano, R.M.¹ Buzby, J.H.² Macropulos, N.³ Springer, J.P.⁴

9
- 0027169494
- (h) Lopez, J. C.; Lameignere, E.; Burnouf, C.; Laborde, M. A.; Ghini, A. A.; Olesker, A.; Lukacs, G. Tetrahedron 1993, 49, 7701.
- (1993) Tetrahedron , vol.49 , pp. 7701
- Lopez, J.C.¹ Lameignere, E.² Burnouf, C.³ Laborde, M.A.⁴ Ghini, A.A.⁵ Olesker, A.⁶ Lukacs, G.⁷

10
- 37049075623
- (a) Lopez, J. C.; Lameignere, E.; Lukacs, G. J. Chem. Soc., Chem. Commun. 1988, 514.
- (1988) J. Chem. Soc., Chem. Commun , pp. 514
- Lopez, J.C.¹ Lameignere, E.² Lukacs, G.³

11
- 0001091013
- (b) Giuliano, R. M.; Jordan, A. D. Jr.; Gauthier, A. D.; Hoogsteen, K. J. Org. Chem. 1993, 58, 4979.
- (1993) J. Org. Chem , vol.58 , pp. 4979
- Giuliano, R.M.¹ Jordan Jr., A.D.² Gauthier, A.D.³ Hoogsteen, K.⁴

12
- 33748220243
- (c) Al-Abed, Y.; Al-Tel, T. H.; Schröder, C.; Voelter, W. Angew. Chem., Int. Ed. Engl. 1994, 33, 1499.
- (1994) Angew. Chem., Int. Ed. Engl , vol.33 , pp. 1499
- Al-Abed, Y.¹ Al-Tel, T.H.² Schröder, C.³ Voelter, W.⁴

13
- 0033570247
- (d) Hayashi, M.; Tsukada, K.; Kawabata, H.; Lamberth, C. Tetrahedron 1999, 55, 12287.
- (1999) Tetrahedron , vol.55 , pp. 12287
- Hayashi, M.¹ Tsukada, K.² Kawabata, H.³ Lamberth, C.⁴

14
- 37049083434
- (a) Dubois, E.; Beau, J. M. J. Chem. Soc., Chem. Commun. 1990, 1191.
- (1990) J. Chem. Soc., Chem. Commun , pp. 1191
- Dubois, E.¹ Beau, J.M.²

15
- 0026848833
- (b) Dubois, E.; Beau, J. M. Carbohydr. Res. 1992, 228, 103.
- (1992) Carbohydr. Res , vol.228 , pp. 103
- Dubois, E.¹ Beau, J.M.²

16
- 67650676563
- (c) Abas, A.; Beddoes, R. L.; Conway, J. C.; Quayle, P.; Urch, C. J. Synlett 1995, 1264.
- (1995) Synlett , pp. 1264
- Abas, A.¹ Beddoes, R.L.² Conway, J.C.³ Quayle, P.⁴ Urch, C.J.⁵

17
- 24044536953
- (d) Koo, B.; McDonald, F. E. Org. Lett. 2005, 7, 3621.
- (2005) Org. Lett , vol.7 , pp. 3621
- Koo, B.¹ McDonald, F.E.²

18
- 33645396218
- (e) Conway, J. C.; Urch, C. J.; Quayle, P.; Xu, J. Synlett 2006, 776.
- (2006) Synlett , pp. 776
- Conway, J.C.¹ Urch, C.J.² Quayle, P.³ Xu, J.⁴

19
- 0030878188
- Nicolaou, K. C.; Shi, G. Q.; Gunzner, J. L.; Gärtner, P.; Yang, Z. J. Am. Chem. Soc. 1997, 119, 5467.
- (1997) J. Am. Chem. Soc , vol.119 , pp. 5467
- Nicolaou, K.C.¹ Shi, G.Q.² Gunzner, J.L.³ Gärtner, P.⁴ Yang, Z.⁵

20
- 14644391471
- Gueyrard, D.; Haddoub, R.; Salem, A.; Said Bacar, N.; Goekjian, P. G. Synlett 2005, 520.
- (2005) Synlett , pp. 520
- Gueyrard, D.¹ Haddoub, R.² Salem, A.³ Said Bacar, N.⁴ Goekjian, P.G.⁵

21
- 33646551219
- Gueyrard, D.; Fontaine, P.; Goekjian, P. G. Synthesis 2006, 1499.
- (2006) Synthesis , pp. 1499
- Gueyrard, D.¹ Fontaine, P.² Goekjian, P.G.³

22
- 0035804972
- Dillep Kumar, J. S.; Dupradeau, F. Y.; Jane Strouse, M.; Phelps, M. E.; Toyokuni, T. J. Org. Chem. 2001, 66, 3220.
- (2001) J. Org. Chem , vol.66 , pp. 3220
- Dillep Kumar, J.S.¹ Dupradeau, F.Y.² Jane Strouse, M.³ Phelps, M.E.⁴ Toyokuni, T.⁵

23
- 35348959095
- Typical Procedure and Selected Data for Compound 9: In a 10-mL round-bottomed flask under argon, 7 (100 mg, 0.16 mmol) and 4-chlorobenzaldehyde (22 μL, 1.2 equiv) were dissolved in freshly distilled THF (1 mL) at -78°C, then a 1 M solution of LiHMDS in THF (383 μL, 2.4 equiv) was added dropwise over 5 min. Stirring was maintained during 30 min at -78°C and then at r.t. for 1 h. After hydrolysis, the mixture was extracted with EtOAc (3 x 10 mL, dried over Na2SO4, concentrated by rotary evaporation and purified by flash chromatography to afford the desired product (63 mg, 0.115 mmol, yield: 72, yellow liquid; [α] D22 -1 (c, 1, acetone, Rf0.44 (EtOAc-PE, 1:9, 1H NMR (300 MHz, CD3COCD3, δ, 3.89-3.96 (m, 3 H, 2 x H-8, H-6, 4.21-4.26 (m, 1 H, H-7, 4.31 (dd, J, 3.3, 5.7 Hz, 1 H, H-5, 4.61-4.88 m, 6 H, OCH2Ph, 5.25
- 4Na: 575.1965; found: 575.1969.

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