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Synthesis of the Potential Mannosidase Inhibitor via 1,3-Dipolar Cycloaddition Involving Cyclic Nitrone and Unsaturated Chiral gamma-Lactone

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Warianty tytułu
Języki publikacji
EN
Abstrakty
EN
The 1,3-dipolar cycloaddition of cyclic nitrone derived from tartaric acid with (S)-5-hydroxymethyl-2(5H)-furanone leads to a single adduct which was transformed into 1,2,6,7-tetrahydroxy-2-hydroxymethyl-indolizidine via reaction sequence involving protection of the hydroxymethyl group, reduction of the lactone moiety, protection of the resulting diol, and the N-O hydrogenolysis followed by the intramolecular alkylation of the nitrogen atom.
Słowa kluczowe
Rocznik
Strony
237--243
Opis fizyczny
Bibliogr. 14 poz., rys.
Twórcy
autor
autor
autor
  • Institute of Organic Chemistry of the Polish Academy of Sciences, Kasprzaka 44/52, 01-224 Warsaw, Poland, chmiel@icho.edu.pl
Bibliografia
  • 1. (a)PearsonM.S.,Mathe-AllainmatM.,Fargeas J. and Lebreton J., Eur.J Org. Chem., 11,2159(2005);(b)    Watson A.A., Fleet G. W. J., Asano N., Molyneux R. J. and Nash R. J., Phytochemistry, 56,265 (2001);(c)     Asano N., Kato A. and Watson A.A., MiniRev. Med Chem., l, 145 (2001).
  • 2. Stütz A., Ed., Iminosugars as Glycosidases Inhibitors: Norjirmycin and Beyond; Wiley-VCH,Weinheim, 1999.
  • 3. (a) Fleet G. W.J., Fellows L.E. and Winchester B., In Bioactive Compounds from Plants; Chadwick P.J.and March J., Eds.; Wiley & Sons: Chichester, 1990; pp. 112-125; (b) Asano N., Nash R.J.,Molyneux R. J. and Fleet G. W. J., Tetrahedron: Asymmetry, 11,1645 (2000); (c) Chapleur Y., Ed., Carbohydrate Mimics, WileyaYCH: Weinheim, 1998; (d) Martin O.R. and Compain Ph., Curr. Top. Med.Chem., 3, 541 (2003); (e) El Nemr A., Tetrahedron, 56, 8579 (2000); (f) Felpin F.-X. and Lebreton J.,Eur. J. Org. Chem., 3693 (2003); (g) Cossy J. and Vogel P., In Stereoselective Synthesis. Part H; Atta-ur-Rahman, Ed.; Elsevier: Amsterdam, 1993; Vol. 12, pp. 275-363; (h) Herczegh P., Kovacs I. And Sztaricskai F., In Chemistry of Biologically Important Hydroxylated Indolizidines: Synthesis of Swainsonine, Castanospermine and Slaframine, Springer, Berlin, 1993; (i) Lukacs G. and Ohno M.,Eds.; Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbiol Products ;Springer: Berlin, 1993; Vol. 2, pp. 751-828; (j) Cipolla L., La Ferla B. and Nicotra F., Curr. Top. Med. Chem., 3,485 (2003); (k) Hohenschutz L.D., Bell E.A., Jewess P.J., Lewerothy D.P., Pryce R.J., Arnold E. and Chardy J., Phytochemistry, 20,811 (l 981); (1) Pastuszak I., Molyneux R.J., James L.F. and Elbien A.D., Biochemistry, 29, 1886 (1990); (m) El Ashry E.S.H. and El Nemr A., Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates;, Blackwell Publishing, Oxford, 2005.
  • 4. Liddell J.R., Nat. Prod. Rep., 14, 653 (1997); 15, 363 (1998); 16, 499 (1999); 17, 455 (2000); 18,441 (2001); 19, 773 (2002).
  • 5. Michael J.P., Nat. Prod. Rep., 14, 619 (1997); 15, 571 (1998); 16, 675 (1999); 17, 579 (2000); 18, m(2001); 19, 719 (2002); 20, 458 (2003); 21, 625 (2004); 22, 603 (2005); 24, 191 (2007).
  • 6. (a) Socha D., Jurczak M. and Chmielewski M., Carbohydr. Res., 336, 315 (2001); (b) Rabiczko J.,Urbańczyk-Lipkowska Z. and Chmielewski M., Tetrahedron, 58,1433 (2002); (c) Socha D., Paśniczek K., Jurczak M., Sołecka J. and Chmielewski M., Carbohydr. Res., 341, 2005 (2006); (d) Paśniczek K.,Socha D., Sołecka J., Jurczak M. and Chmielewski M., Can. J. Chem., 84, 534 (2006); (e) Panfil L,Sołecka J. and Chmielewski M., J. Carbohydr. Chem., 25, 673 (2006); (f) Paśniczek K., Sołecka J. and  Chmielewski  M.,  J.   Carbohydr.   Chem.,  26,   195   (2007);   (g)   Stecko   S.,   Jurczak M.,Urbańczyk-Lipkowska Z., Sołecka J. and Chmielewski M., Carbohydr. Res., 3
  • 7. (a) Goti A., Cicchi S., Fedi V., Nannelli L. and Brandi A., J. Org. Chem., 62,3119 (l 997); (b) Cicchi S.,Goti A. and Brandi A., J. Org. Chem., 60, 4743 (1995); (c) Cicchi S., Hold I. and Brandi A., J. Org.Chem.,58,5274(1993).
  • 8. (a) Paśniczek K., Socha D., Jurczak M., Frelek J., Suszczyńska A., Urbańczyk-Lipkowska Z. and Chmielewski M., J. Carbohydr. Chem., 22,613 (2003); (b) Socha D., Jurczak M., Frelek J., Klimek A.,Rabiczko J., Urbańczyk-Lipkowska Z., Suwińska K., Chmielewski M., Cardona F., Goti A. and Brandi A., Tetrahedron: Asymmetry, 12, 3163 (2001); (c) Jurczak M., Rabiczko J., Socha D.,Chmielewski M., Cardona F., Goti A. and Brandi A., Tetrahedron: Asymmetry, 11, 2015 (2000).
  • 9. (a) Stecko S., Paśniczek K., Jurczak M., Urbańczyk-Lipkowska Z. and Chmielewski M., Tetrahedron: Asymmetry, 17, 68 (2006); (b) Stecko S., Paśniczek K., Jurczak M., Urbańczyk-Lipkowska Z. and Chmielewski M., Tetrahedron: Asymmetry, 18, 1085 (2007); (c) Stecko S., Paśniczek K., Michel C., Milet A., Perez S. and Chmielewski M., Tetrahedron: Asymmetry, 19, 1660 (2008); (d) Stecko S.,Paśniczek K., Michel C., Milet A., Perez S. and Chmielewski M., Tetrahedron: Asymmetry, 19, 2140 (2008).
  • 10. Niva T., Inouye S., Tsuruoka T., Koaze Y. and Niida T., Agric. Biol. Chem., 34, 966 (1970).
  • ll. Tsuruoka T., Fukuyasu H., Ishii M., Usui T., Shibahara S. and Inouve S., J. Antibiot., 49, 151 (1996).
  • 12. Leger G.,Adv. Carbohydr. Chem. Biochem., 48, 319 (1990).
  • 13. Rausher E., In Methods of Enzymatic Analysis, 3rd ed., Bergmeyer H.U., Ed.; VCH Publications: Weinheim, 1984; Vol. 4, pp. 152-161.
  • 14. Armarego W.L.F. and Chai C.L.L., Purification of Laboratory Chemicals, 5th ed.; Butterwoth-Heinemann, Burlington, 2003.
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ5-0024-0066
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