Total, asymmetric synthesis of ethyl d-ido-4-heptulosuronate derivatives starting from diethyl 4-oxopimelate

Author:

Lemaire-Audoire Sandrine,Vogel Pierre

Publisher

Elsevier BV

Subject

Inorganic Chemistry,Organic Chemistry,Physical and Theoretical Chemistry,Catalysis

Reference17 articles.

1. Lemaire-Audoire, S.; Vogel, P. Tetrahedron Lett. 1998, 39, 1345–1348.

2. Pettit, G. R. Pure Appl. Chem. 1994, 66, 2271–2281; Pietruszka, J. Angew. Chem., Int. Ed. Engl. 1998, 37, 2629–2636 and references cited therein.

3. Heptoses are found in the lipopolysaccharides of many microorganisms, see for example: Adams, G. A.; Young, R. Ann. New York Acad. Sci. 1966, 133, 527–545; Dmitriev, B. A.; Hinton, N. A.; Lowe, R. W.; Jones, J. K. Can. J. Microbiol. 1971, 17, 1385–1394; Weckesser, J.; Drews, G.; Roppel, J.; Mayer, H.; Fromme, I. Archiv. Microbiology 1974, 101, 233–245; Kotelko, K.; Gromska, W.; Papierz, M.; Sidorczyk, Z.; Krajewska, M.; Szer, K. J. Hygiene, Epidemiol., Microbiol., Immunol. 1977, 21, 271–284; Holst, O.; Zähringer, U.; Brade, H.; Zamojski, A. Carbohydr. Res. 1991, 215, 323–335; Hofinger, A.; Kosma, P.; Christian, R.; Bock, K.; Brade, H. Ibid. 1993, 243, 273–291; Kondo, S.; Watabe, T.; Haishima, Y.; Hisatsune, K. Ibid. 1993, 245, 361–365; Schweda, E. K. H.; Hegedus, O. E.; Borrelli, S.; Lindberg, A. A.; Weiser, J. N.; Maskell, D. J.; Moxon, E. R. Ibid. 1993, 246, 319–330; Lebbar, S.; Caroff, M.; Szabó, L.; Mérionne, C.; Szilógyi, L. Ibid. 1994, 259, 257–275; Beckmann, F.; Moll, H.; Jäger, K.-E.; Zähringer, U. Ibid. 1995, 267, C3; Aspinall, G. O.; Monteiro, M. A.; Pang, H. Ibid. 1995, 279, 245–264; Toman, R.; Skultéty, L. Ibid. 1996, 283, 175–185; Mahbuhur Rahman, M.; Stephens, D. S.; Kahler, C. M.; Glushka, J.; Carlson, R. W. Carbohydr. Res. 1998, 307, 311–324; Kosma, P.; Wugeditsch, T.; Christian, R.; Zayni, S.; Messner, P. Glycobiology 1995, 5, 791–796; Gabriel, J. Chem. Listy 1992, 86, 95.

4. 4-Amino-4-deoxy-l-glycero-l-manno-pyranose is the sugar moiety of spicamycin and analogues, nucleosides with anti-tumor activity, see for example: Hayakawa, Y.; Nakagawa, M.; Kawai, H.; Tanabe, K.; Nakayama, H.; Shimazu, A.; Seto, H.; Otake, N. J. Antibiotics 1983, 36, 934–937; Sakai, T.; Kawai, H.; Kamishohara, M.; Odagawa, A.; Suzuki, A.; Uchida, T.; Kawasaki, T.; Tsurdo, T.; Otake, N. Ibid. 1995, 48, 504–508.

5. Dondoni, A.; Fantin, G.; Fogagnolo, F.; Medici, A.; Pedrini, P. J. Org. Chem. 1989, 54, 702–706; Anzeveno, P. B.; Creemer, Z. J.; Daniel, J. K.; King, C.-H. R.; Liu, P. S. Ibid. 1989, 54, 2539–2542; Greszczyk, B.; Holst, O.; Müller-Loennies, S.; Zamojski, A. Carbohydr. Res. 1998, 307, 55–67; Stêpowska, H.; Zamojski, A. Ibid. 1997, 304, 347–358; Boons, G. J. P. H.; Van der Marel, G. A.; Van Boom, J. H. Tetrahedron Lett. 1989, 30, 229–232; Boons, G. J. P. H.; Overhand, M.; Van der Marel, G. A.; Van Boom, J. H. Angew. Chem., Int. Ed. Engl. 1989, 28, 1504–1506; Dasser, M.; Chrétien, F.; Chapleur, Y. J. Chem. Soc., Perkin Trans. 1 1990, 3091–3094; Bichard, C. J. F.; Wheatley, J. R.; Fleet, G. W. J. Tetrahedron: Asymmetry 1994, 5, 431–440; Brimacombe, J. S.; Kabir, A. K. M. S. Carbohydr. Res. 1987, 169, 234–240; Gubernator, K.; Kennard, C. H. L.; Schönholzer, P.; Weller, T. J. Chem. Soc., Chem. Commun. 1988, 14–16; Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B. Tetrahedron Lett. 1988, 29, 693–696.

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