Synthesis of β-D-galactosyl ceramide methylene isostere

Journal of Organic Chemistry

Volumn 64, Issue 15, 1999, Pages 5557-5564

  Dondoni, Alessandro ^a   Perrone, Daniela ^a   Turturici, Elisa ^a  

^a UNIVERSITY OF FERRARA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BETA DEXTRO GALACTOSYL CERAMIDE METHYLENE ISOSTERE; CERAMIDE; GLYCOSPHINGOLIPID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; GEOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REDUCTION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033597811     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo990398l     Document Type: Article

References (77)

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2. For C-disaccharides, see: (a) Wang, Y.; Goekjian, P. G.; Ryckman, D. M.; Miller, W. H.; Babirad, S. A.; Kishi, Y. J. Org. Chem. 1992, 57, 482-489. (b) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975-981. (c) Mallet, A.; Mallet, J. M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593-2608. (d) Skrydstrup, T.; Mazéas, D.; Elmouchir, M.; Doisneau, G.; Riche, C.; Chiaroni, A.; Beau, J. M. Chem. Eur. J. 1997, 3, 1342-1356. (e) Dondoni, A.; Zuurmond, H. M.; Boscarato A. J. Org. Chem. 1997, 62, 8114-8124. For C-trisaccharides, see: (f) Haneda, T.; Goekjian, P. G.; Kim, S. H.; Kishi, Y. J. Org. Chem. 1992, 57, 490-498. (g) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802-9803. (h) Sutherlin, D. P.; Armstrong, R. W. J. Org. Chem. 1997, 62, 5267-5283. For (1→6)-C-oligosaccharides, see: (i) Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Tetrahedron Lett. 1998, 39, 7991-7994.
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4. For C-disaccharides, see: (a) Wang, Y.; Goekjian, P. G.; Ryckman, D. M.; Miller, W. H.; Babirad, S. A.; Kishi, Y. J. Org. Chem. 1992, 57, 482-489. (b) Dietrich, H.; Schmidt, R. R. Liebigs Ann. Chem. 1994, 975-981. (c) Mallet, A.; Mallet, J. M.; Sinaÿ, P. Tetrahedron: Asymmetry 1994, 5, 2593-2608. (d) Skrydstrup, T.; Mazéas, D.; Elmouchir, M.; Doisneau, G.; Riche, C.; Chiaroni, A.; Beau, J. M. Chem. Eur. J. 1997, 3, 1342-1356. (e) Dondoni, A.; Zuurmond, H. M.; Boscarato A. J. Org. Chem. 1997, 62, 8114-8124. For C-trisaccharides, see: (f) Haneda, T.; Goekjian, P. G.; Kim, S. H.; Kishi, Y. J. Org. Chem. 1992, 57, 490-498. (g) Sutherlin, D. P.; Armstrong, R. W. J. Am. Chem. Soc. 1996, 118, 9802-9803. (h) Sutherlin, D. P.; Armstrong, R. W. J. Org. Chem. 1997, 62, 5267-5283. For (1→6)-C-oligosaccharides, see: (i) Dondoni, A.; Kleban, M.; Zuurmond, H.; Marra, A. Tetrahedron Lett. 1998, 39, 7991-7994.
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22. Synthetic methods for glycosphingolipids have been reviewed: (a) Gigg, J.; Gigg, R. Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 154, pp 77-139. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; M. Dekker: New York, 1997; pp 357-379. For selected recent papers, see: (c) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693-3695. (d) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314. (e) Gervay, J.; Peterson, J. M.; Oriyama, T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 5465-5468. (f) Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840- 7841. (g) Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359- 1362. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001. (i) Wilstermann, M.; Magnusson, G. J. Org. Chem. 1997, 62, 7961-7971. (j) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524-1528. (k) Takikawa, H.; Muto, S.; Mori, K. Tetrahedron 1998, 54, 3141-3150.
23. Synthetic methods for glycosphingolipids have been reviewed: (a) Gigg, J.; Gigg, R. Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 154, pp 77-139. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; M. Dekker: New York, 1997; pp 357-379. For selected recent papers, see: (c) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693-3695. (d) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314. (e) Gervay, J.; Peterson, J. M.; Oriyama, T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 5465-5468. (f) Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840- 7841. (g) Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359- 1362. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001. (i) Wilstermann, M.; Magnusson, G. J. Org. Chem. 1997, 62, 7961-7971. (j) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524-1528. (k) Takikawa, H.; Muto, S.; Mori, K. Tetrahedron 1998, 54, 3141-3150.
24. Synthetic methods for glycosphingolipids have been reviewed: (a) Gigg, J.; Gigg, R. Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 154, pp 77-139. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; M. Dekker: New York, 1997; pp 357-379. For selected recent papers, see: (c) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693-3695. (d) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314. (e) Gervay, J.; Peterson, J. M.; Oriyama, T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 5465-5468. (f) Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840- 7841. (g) Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359- 1362. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001. (i) Wilstermann, M.; Magnusson, G. J. Org. Chem. 1997, 62, 7961-7971. (j) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524-1528. (k) Takikawa, H.; Muto, S.; Mori, K. Tetrahedron 1998, 54, 3141-3150.
25. Synthetic methods for glycosphingolipids have been reviewed: (a) Gigg, J.; Gigg, R. Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 154, pp 77-139. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; M. Dekker: New York, 1997; pp 357-379. For selected recent papers, see: (c) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693-3695. (d) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314. (e) Gervay, J.; Peterson, J. M.; Oriyama, T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 5465-5468. (f) Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840- 7841. (g) Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359- 1362. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001. (i) Wilstermann, M.; Magnusson, G. J. Org. Chem. 1997, 62, 7961-7971. (j) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524-1528. (k) Takikawa, H.; Muto, S.; Mori, K. Tetrahedron 1998, 54, 3141-3150.
26. Synthetic methods for glycosphingolipids have been reviewed: (a) Gigg, J.; Gigg, R. Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 154, pp 77-139. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; M. Dekker: New York, 1997; pp 357-379. For selected recent papers, see: (c) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693-3695. (d) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314. (e) Gervay, J.; Peterson, J. M.; Oriyama, T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 5465-5468. (f) Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840- 7841. (g) Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359- 1362. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001. (i) Wilstermann, M.; Magnusson, G. J. Org. Chem. 1997, 62, 7961-7971. (j) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524-1528. (k) Takikawa, H.; Muto, S.; Mori, K. Tetrahedron 1998, 54, 3141-3150.
27. Synthetic methods for glycosphingolipids have been reviewed: (a) Gigg, J.; Gigg, R. Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 154, pp 77-139. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; M. Dekker: New York, 1997; pp 357-379. For selected recent papers, see: (c) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693-3695. (d) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314. (e) Gervay, J.; Peterson, J. M.; Oriyama, T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 5465-5468. (f) Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840-7841. (g) Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359- 1362. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001. (i) Wilstermann, M.; Magnusson, G. J. Org. Chem. 1997, 62, 7961-7971. (j) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524-1528. (k) Takikawa, H.; Muto, S.; Mori, K. Tetrahedron 1998, 54, 3141-3150.
28. Synthetic methods for glycosphingolipids have been reviewed: (a) Gigg, J.; Gigg, R. Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 154, pp 77-139. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; M. Dekker: New York, 1997; pp 357-379. For selected recent papers, see: (c) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693-3695. (d) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314. (e) Gervay, J.; Peterson, J. M.; Oriyama, T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 5465-5468. (f) Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840- 7841. (g) Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359-1362. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001. (i) Wilstermann, M.; Magnusson, G. J. Org. Chem. 1997, 62, 7961-7971. (j) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524-1528. (k) Takikawa, H.; Muto, S.; Mori, K. Tetrahedron 1998, 54, 3141-3150.
29. Synthetic methods for glycosphingolipids have been reviewed: (a) Gigg, J.; Gigg, R. Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 154, pp 77-139. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; M. Dekker: New York, 1997; pp 357-379. For selected recent papers, see: (c) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693-3695. (d) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314. (e) Gervay, J.; Peterson, J. M.; Oriyama, T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 5465-5468. (f) Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840- 7841. (g) Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359- 1362. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001. (i) Wilstermann, M.; Magnusson, G. J. Org. Chem. 1997, 62, 7961-7971. (j) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524-1528. (k) Takikawa, H.; Muto, S.; Mori, K. Tetrahedron 1998, 54, 3141-3150.
30. Synthetic methods for glycosphingolipids have been reviewed: (a) Gigg, J.; Gigg, R. Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 154, pp 77-139. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; M. Dekker: New York, 1997; pp 357-379. For selected recent papers, see: (c) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693-3695. (d) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314. (e) Gervay, J.; Peterson, J. M.; Oriyama, T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 5465-5468. (f) Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840- 7841. (g) Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359- 1362. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001. (i) Wilstermann, M.; Magnusson, G. J. Org. Chem. 1997, 62, 7961-7971. (j) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524-1528. (k) Takikawa, H.; Muto, S.; Mori, K. Tetrahedron 1998, 54, 3141-3150.
31. Synthetic methods for glycosphingolipids have been reviewed: (a) Gigg, J.; Gigg, R. Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 154, pp 77-139. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; M. Dekker: New York, 1997; pp 357-379. For selected recent papers, see: (c) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693-3695. (d) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314. (e) Gervay, J.; Peterson, J. M.; Oriyama, T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 5465-5468. (f) Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840- 7841. (g) Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359- 1362. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001. (i) Wilstermann, M.; Magnusson, G. J. Org. Chem. 1997, 62, 7961-7971. (j) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524-1528. (k) Takikawa, H.; Muto, S.; Mori, K. Tetrahedron 1998, 54, 3141-3150.
32. Synthetic methods for glycosphingolipids have been reviewed: (a) Gigg, J.; Gigg, R. Topics in Current Chemistry; Springer-Verlag: Berlin, Heidelberg, 1990; Vol. 154, pp 77-139. (b) Hasegawa, A.; Kiso, M. In Preparative Carbohydrate Chemistry; Hanessian S., Ed.; M. Dekker: New York, 1997; pp 357-379. For selected recent papers, see: (c) Nicolaou, K. C.; Caulfield, T. J.; Kataoka, H.; Stylianides, N. A. J. Am. Chem. Soc. 1990, 112, 3693-3695. (d) Peterson, M. A.; Polt, R. J. Org. Chem. 1993, 58, 4309-4314. (e) Gervay, J.; Peterson, J. M.; Oriyama, T.; Danishefsky, S. J. J. Org. Chem. 1993, 58, 5465-5468. (f) Bilodeau, M. T.; Park, T. K.; Hu, S.; Randolph, J. T.; Danishefsky, S. J.; Livingston, P. O.; Zhang, S. J. Am. Chem. Soc. 1995, 117, 7840- 7841. (g) Liu, K. K.-C.; Danishefsky, S. J. Chem. Eur. J. 1996, 2, 1359- 1362. (h) Castro-Palomino, J. C.; Ritter, G.; Fortunato, S. R.; Reinhardt, S.; Old, L. J.; Schmidt, R. R. Angew. Chem., Int. Ed. Engl. 1997, 36, 1998-2001. (i) Wilstermann, M.; Magnusson, G. J. Org. Chem. 1997, 62, 7961-7971. (j) Kamitakahara, H.; Suzuki, T.; Nishigori, N.; Suzuki, Y.; Kanie, O.; Wong, C.-H. Angew. Chem., Int. Ed. Engl. 1998, 37, 1524-1528. (k) Takikawa, H.; Muto, S.; Mori, K. Tetrahedron 1998, 54, 3141-3150.
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