Synthesis and application of N-methoxy-N-methyl-2-phenylsulfonyl- acetamide as a two-carbon homologating agent

Synthesis

Volumn , Issue 3, 2000, Pages 375-382

  Satyamurthi, N ^a   Singh, Jaimala ^b   Aidhen, Indrapal Singh ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

^b CENTRAL LEATHER RESEARCH INSTITUTE   (India)

Author keywords

(+) aspicillin; Alkylations; Desulfonylation; Higher 2,3 dideoxy sugars; Sulfones; Two carbon homologation; Weinreb amides

Indexed keywords

ACETAMIDE DERIVATIVE; DEOXYSUGAR; SULFONE DERIVATIVE;

ALKYLATION; ARTICLE; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0034050744     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6337     Document Type: Article

References (35)

1. Nahm, S.; Weinreb, S. M. Tetrahedron Lett. 1981, 22, 3815.
2. For recent reviews on Weinreb amides; see: (a) Sibi, M. P. Org. Prep. Proced. Intl. 1993, 25, 15.
3. (b) Mentzel, M.; Hoffmann, H. M. R. J. Prakt. Chem. 1997, 339, 517.
4. For representative examples; see: (a) Hamada, Y.; Yokokawa, F.; Kabeya, M.; Hatano, K.; Kurono, Y.; Shiori, T. Tetrahedron 1996, 52, 8297.
5. (b) Meyer, S. D.; Miwa, T.; Nakatsuka, M; Schreiber, S. L. J. Org. Chem. 1992, 57, 5058.
6. (c) Marshall, J. A.; Seletsky, B. M.; Luke, G. P. J. Org. Chem. 1994, 59, 3413.
7. (d) Overhand, M.; Hecht, S. M. J. Org. Chem. 1994, 59, 4721.
8. Evans, D. A.; Kaldor, S. W.; Jones, T. K.; Clardy, J.; Stout, T. J. J. Am. Chem. Soc. 1990, 112, 7001.
9. Netz, D. F.; Siedel, J. L. Tetrahedron Lett. 1992, 33, 1957.
10. Nullizard, J. M.; Boumendjel, A.; Massiot, G.; Tetrahedron Lett. 1989, 30, 3779.
11. (a) Schwarz, K.; Neef, G.; Kirsch, G.; Fahrnow, A. M.; Steinmeyer, A. Tetrahedron 1995, 51, 9543.
12. (b) Hanessian, S.; Fu, J.M.; Chiara, J. L.; Di Fabio, R. Tetrahedron Lett. 1993, 34, 4157.
13. Hoffmann, H. M. R.; Weichert, A. J. Org. Chem. 1991, 56, 4098, and references cited therein.
14. (a)Thomsen, M. W.; Handwerker, B. M.; Katz, S. A.; Fisher, S. A. Synth.Commun. 1988, 18, 1433.
15. (b) Ono, N.; Tamura, R.; Tanikaga, R.; Kaji, A. Synthesis 1977, 690.
16. (c) Trost, B.M.; Verhoeven, T.R. J. Am. Chem. Soc. 1977, 99, 3867.
17. Najera, C.; Yus, M. Tetrahedron 1999, 55, 10547.
18. (a) Graham, S.L.; Scholz, T. H. J. Org.Chem. 1991, 56, 4260.
19. (b) Graham, S.L.; Scholz, T. H. Tetrahedron Lett. 1990, 31, 6269.
20. Tillyer, R.; Frey, L. F.; Tshaen, D. M.; Dolling, U-H. Synlett 1996, 225.
21. Trost, B. M.; Arndt, H. C.; Strege, P. E.; Verhoeven, T. R. Tetrahedron Lett. 1976, 39, 3477.
22. Bartinicka, E.; Zamonski, A. Polish J. Chem. 1998, 72, 688.
23. Jung, M. E.; Shaw, T. J. J. Am. Chem. Soc. 1980, 102, 6304.
24. Plaintier-Rayon, R.; Portella, C. Tetrahedron Lett. 1996, 37, 6113.
25. For the two carbon homologation of sugar aldehydes using Wittig based reagents, see: Dondoni, A.; Merino, P.; Orduna, J.; Perrone, D. Synthesis 1993, 277.
26. Gerspacher, M.; Rapoport, H. J. Org. Chem. 1991, 56, 3700.
27. Several synthetic efforts have been made towards the C-3-C-9 fragment of aspicillin, see: Chenevert, R.; Lavoie, M.; Dasser, M. Can. J. Chem. 1997, 75, 68, and references cited therein.
28. 6g: Einhorn, J; Einhorn, C.; Luche, J-L. Synth. Commun. 1990, 20, 1105. 6i: Kotsuki, H.; Ushio, Y.; Kadota, I.; Ochi, M. J. Org. Chem. 1989, 54, 5153.
29. 6g: Einhorn, J; Einhorn, C.; Luche, J-L. Synth. Commun. 1990, 20, 1105. 6i: Kotsuki, H.; Ushio, Y.; Kadota, I.; Ochi, M. J. Org. Chem. 1989, 54, 5153.
30. 8a: Molander, G. A.; Wolfe, J.P. J. Braz. Chem. Soc. 1996, 7, 335; Chem. Abstr. 1996, 125, 300-440. 8b: Molander, G. A.; Losada, C. P. J. Org. Chem. 1997, 62, 2935. 8c: Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421. 8d: Williams, J. M.; Jobson, R. B.; Yasuda, U.; Marchesini, G.; Dolling, U-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461. 8e: Nitz, T. J.; Volkots, D. L.; Aldous, D. J.; Oglesby, R. C. J. Org. Chem. 1994, 59, 5828.
31. 8a: Molander, G. A.; Wolfe, J.P. J. Braz. Chem. Soc. 1996, 7, 335; Chem. Abstr. 1996, 125, 300-440. 8b: Molander, G. A.; Losada, C. P. J. Org. Chem. 1997, 62, 2935. 8c: Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421. 8d: Williams, J. M.; Jobson, R. B.; Yasuda, U.; Marchesini, G.; Dolling, U-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461. 8e: Nitz, T. J.; Volkots, D. L.; Aldous, D. J.; Oglesby, R. C. J. Org. Chem. 1994, 59, 5828.
32. 8a: Molander, G. A.; Wolfe, J.P. J. Braz. Chem. Soc. 1996, 7, 335; Chem. Abstr. 1996, 125, 300-440. 8b: Molander, G. A.; Losada, C. P. J. Org. Chem. 1997, 62, 2935. 8c: Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421. 8d: Williams, J. M.; Jobson, R. B.; Yasuda, U.; Marchesini, G.; Dolling, U-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461. 8e: Nitz, T. J.; Volkots, D. L.; Aldous, D. J.; Oglesby, R. C. J. Org. Chem. 1994, 59, 5828.
33. 8a: Molander, G. A.; Wolfe, J.P. J. Braz. Chem. Soc. 1996, 7, 335; Chem. Abstr. 1996, 125, 300-440. 8b: Molander, G. A.; Losada, C. P. J. Org. Chem. 1997, 62, 2935. 8c: Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421. 8d: Williams, J. M.; Jobson, R. B.; Yasuda, U.; Marchesini, G.; Dolling, U-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461. 8e: Nitz, T. J.; Volkots, D. L.; Aldous, D. J.; Oglesby, R. C. J. Org. Chem. 1994, 59, 5828.
34. 8a: Molander, G. A.; Wolfe, J.P. J. Braz. Chem. Soc. 1996, 7, 335; Chem. Abstr. 1996, 125, 300-440. 8b: Molander, G. A.; Losada, C. P. J. Org. Chem. 1997, 62, 2935. 8c: Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421. 8d: Williams, J. M.; Jobson, R. B.; Yasuda, U.; Marchesini, G.; Dolling, U-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461. 8e: Nitz, T. J.; Volkots, D. L.; Aldous, D. J.; Oglesby, R. C. J. Org. Chem. 1994, 59, 5828.
35. 8a: Molander, G. A.; Wolfe, J.P. J. Braz. Chem. Soc. 1996, 7, 335; Chem. Abstr. 1996, 125, 300-440. 8b: Molander, G. A.; Losada, C. P. J. Org. Chem. 1997, 62, 2935. 8c: Trost, B. M.; Shi, Y. J. Am. Chem. Soc. 1993, 115, 9421. 8d: Williams, J. M.; Jobson, R. B.; Yasuda, U.; Marchesini, G.; Dolling, U-H.; Grabowski, E. J. J. Tetrahedron Lett. 1995, 36, 5461. 8e: Nitz, T. J.; Volkots, D. L.; Aldous, D. J.; Oglesby, R. C. J. Org. Chem. 1994, 59, 5828.