[KSCI] Korea Science Citation Index Service

http://dx.doi.org/10.5012/bkcs.2012.33.11.3554

Total Synthesis of Azasugar 1,4-Dideoxy-1,4-imino-D-galacitol

Sadhu, Partha Sarathi (Crop Protection Chemicals Division, Indian Institute of Chemical Technology)
Santhoshi, Amlipur (Crop Protection Chemicals Division, Indian Institute of Chemical Technology)
Rao, Vaidya Jayathirtha (Crop Protection Chemicals Division, Indian Institute of Chemical Technology)

Publication Information

Bulletin of the Korean Chemical Society / v.33, no.11, 2012 , pp. 3554-3558 More about this Journal

Abstract

A new highly stereoselective synthesis of pyrrolidine azasugar 1,4-dideoxy-1,4-imino-D-galacitol is being reported herein. The synthesis was achieved in a linear sequence and inexpensive chiral source (+)-diethyl tartarate was used as the starting material. The key step involved during the synthesis was Pd catalysed amino cyclization of alkenylamine, Bose modified Mitsunobu reaction and Sharpless asymmetric dihydroxylation.

Keywords

Azasugar; 1,4-Dideoxy-1,4-imino-D-galacitol; E. coli K12 UDP-Gal mutase inhibitor; Pd catalysed amino cyclization;

Citations & Related Records

Times Cited By Web Of Science : 0 (Related Records In Web of Science)

Reference

1	Butters, D. T.; van den Broek, A. G. M. L.; Fleet, W. J. G.; Krulle, M. T.; Wormald, R. M.; Dwek, A. R.; Platt, M. F. Tetrahedron: Asymm. 2000, 11, 113. DOI ScienceOn
2	Compain, P.; Martin, O. R. Iminosugars: From Synthesis to Therapeutic Applications; Wiley: Chichester, 2007.
3	Cox, T. M.; Platt, F. M.; Aerts, J. M. F. G. Iminosugars 2007, 295. DOI
4	Winchester, B. G. Tetrahedron: Asymm. 2009, 20, 645. DOI ScienceOn
5	Greimel, P.; Spreitz, J.; Stütz, A. E.; Wrodnigg, T. M. Curr. Topics Med. Chem. 2003, 3, 513. DOI ScienceOn
6	Fattorusso, E.; Scafati, O. T. Modern Alkaloids; Wiley-VCH: New York, 2008; pp 111-133.
7	Look, G. C.; Fotsch, C. H.; Wong, C.-H. Acc. Chem. Res. 1993, 26, 182. DOI ScienceOn
8	Asano, N.; Oseki, K.; Kizu, H.; Matsui, K. J. Med. Chem. 1994, 37, 3701. DOI ScienceOn
9	Cox, T.; Lachmann, R.; Hollak, C.; Aerts, J.; van Weely, S.; Hribicek, M.; Platt, F.; Butters, T.; Dwek, R.; Moyses, C.; Gow, I.; Elstein, D.; Zimran, A. Lancet 2000, 355, 1481. DOI ScienceOn
10	Futerman, A. H.; van Meer, G. Nature Rev. Mol. Cell Biol. 2004, 5, 554. DOI ScienceOn
11	Huang, Y.; Dalton, D. R.; Carroll, P. J. J. Org. Chem. 1997, 62, 372. DOI ScienceOn
12	Meng, Q.; Hesse, M. Helv. Chim. Acta 1991, 74, 445. DOI
13	Fleet, G. W. J.; Nicholas, S. J.; Smith, P. W.; Evans, S. V.; Fellows, L. E.; Nash, R. J. Tetrahedron Lett. 1985, 26, 3127. DOI ScienceOn
14	Lundt, I.; Madsen, R.; Daher, S. A.; Winchester, B. Tetrahedron 1994, 50, 7513. DOI ScienceOn
15	Lee, R. E.; Smith, M. D.; Nash, R. J.; Griffiths, R. C.; McNeil, M.; Grewal, R. K.; Yan, W.; Besra, G. S.; Brennan, P. J.; Fleet, G. W. J. Tetrahedron Lett. 1997, 38, 6733. DOI ScienceOn
16	Sadhu, P. S.; Naveen Kumar, S.; Chandrasekharam, M.; Pica- Mattoccia, L.; Ciol, D.; Jayathirtha Rao, V. Bioorg. Med. Chem. Lett. 2012, 22, 1103. DOI ScienceOn
17	Narender, P.; Srinivas, U.; Ravinder, M.; Anand Rao, B.; Ramesh, Ch.; Harakishore, K.; Gangadasu, B.; Murthy, U. S. N.; Jayathirtha Rao, V. Bioorg. Med. Chem. 2006, 14, 4600. DOI ScienceOn
18	Narender, P.; Srinivas, U.; Gangadasu, B.; Biswas, S.; Jayathirtha Rao, V. Chem. Lett. 2005, 15, 5378. DOI ScienceOn
19	Bernotas, R. C. Tetrahedron Lett. 1990, 31, 469. DOI ScienceOn
20	Pham-Huu, D.-P.; Gizaw, Y.; BeMiller, J. N.; Petrus, L. Tetrahedron 2003, 59, 9413. DOI ScienceOn
21	Wu, S.-F.; Ruan, Y.-P.; Zheng, X.; Huang, P.-Q. Tetrahedron 2010, 66, 1653. DOI ScienceOn
22	Fuentes, J.; Sayago, F. J.; Illangua, J. M.; Gasch, C.; Angulo, M.; Pradera, M. A. Tetrahedron: Asymm. 2004, 15, 603. DOI ScienceOn
23	Lundt, I.; Madsen, R. Synthesis 1993, 720.
24	Lombardo, M.; Fabbroni, S.; Trombini, C. J. Org. Chem. 2001, 66, 1264. DOI ScienceOn
25	Mukai, C.; Moharram, S. M.; Kataoka, O.; Hanaoka, M. J. Chem. Soc. Perkin Trans., 1 1995, 2849.
26	Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651. DOI ScienceOn
27	Harcken, C.; Martin, S. F. Org. Lett. 2001, 3, 3591. DOI ScienceOn
28	Lal, B.; Pramanik, B. N.; Manhas, M. S.; Bose, A. K. Tetrahedron Lett. 1977, 18, 1977. DOI ScienceOn
29	Staudinger, H.; Meyer, J. Helv. Chim. Act. 1919, 2, 635. DOI
30	Gololobov, Yu. G.; Zhmurova, I. N.; Kasukhin, L. F. Tetrahedron 1981, 37, 437. DOI ScienceOn
31	Hirai, Y.; Terada, T.; Momose, T. Tetrahedron Lett. 1992, 33, 7893. DOI ScienceOn
32	Yokoyama, H.; Otaya, K.; Kobayashi, H.; Miyazawa, M.; Yamaguchi, S.; Hirai, Y. Org. Lett. 2000, 2, 2427. DOI ScienceOn
33	Saitoh, Y.; Moriyama, Y.; Hirota, H.; Takahashi, T.; Khuong-Huu, Q. Bull. Chem. Soc. Jpn. 1981, 54, 488. DOI
34	Tamaru, Y.; Hojo, M.; Yoshida, Z. J. Org. Chem. 1988, 53, 5731. DOI
35	Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B. Chem. Rev. 1994, 94, 2483. DOI ScienceOn
36	Jacobsen, E. N.; Marko, I.; Mungall, W. S.; Schroeder, G.; Sharpless, K. B. J. Am. Chem. Soc. 1988, 110, 1968. DOI