Synthesis of An Advanced Precursor to the Amino Epimer of (+)-Pyloricidins

Monatshefte fur Chemie

Volumn 134, Issue 12, 2003, Pages 1617-1622

  Tang, Chao Jun ^a   Shen, Xin ^a   Wu, Yikang ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Acylation; Amino acids; Azides; Carbohydrates; Drugs

Indexed keywords

3 [5 AZIDO 2,3,4,6 TETRAKIS(BENZYLOXY)HEXANOYLAMINO] 3 PHENYLPROPIONATE; BACTERIAL PROTEIN; GALACTOSE; PROPIONIC ACID DERIVATIVE; PYLORICIDIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; EPIMER; PRECURSOR; SYNTHESIS;

EID: 0348107391     PISSN: 00269247     EISSN: None     Source Type: Journal    
DOI: 10.1007/s00706-003-0094-1     Document Type: Article

References (22)

1. a) Nakao M, Miyagawa K-I, Nakano Y, Sakane T, Tada M, Nishimura O, Fujino M (2001) J Antibiot 54: 926;
2. b) Nagano Y, Ikedo K, Fujishima A, Izawa M, Tsubotani S, Nishimura O, Fujino M (2001) J Antibiot 54: 934
3. Warren JR, Marshall BJ (1983) Lancet 1273
4. a) Graham DY (1993) N Engl J Med 328: 249;
5. b) Mannes GA, Bayerdorffer E, Höchter W, Weingart J, Heldwein W, Sommer A, Muller-Lissner S, Boenschein W, Weinzierl M, Ruckdeschel G, Blendinger C, von Wulffen H, Köpcke W, Stolte M (1993) Eur J Gastroenterol Hepatol 5: 145
6. a) Talley NJ, Zinsmeister AR, Weaver A, DiMagno EP, Carpenter HA, Perez-Perez GI, Blaser MJ (1991) J Natl Cancer Inst 83: 1734;
7. b) Watanabe T, Tada M, Hagai H, Sasaki S, Nakao M (1998) Gastroenterology 115: 642;
8. c) Blaser MJ (2000) Nature: Medicine 6: 376
9. Hasuoka A, Nishikimi Y, Nakayama Y, Kamiyama K, Nakao M, Miyagawa K-I, Nishimura O, Fujino M (2002) J Antibiot 55: 191
10. a) Hasuoka A, Nishikimi Y, Nakayama Y, Kamiyama K, Nakao M, Miyagawa K-I, Nishimura O, Fujino M (2002) J Antibiot 55: 322;
11. b) Hasuoka A, Nishikimi Y, Nakayama Y, Kamiyama K, Nakao M, Miyagawa K-I, Nishimura O, Fujino M (2002) J Antibiot 55: 499
12. Goebel M, Nothofer H-G, Ross G, Ugi I (1997) Tetrahedron 53: 3123
13. Wardrop DJ, Zhang W, Fritz J (2002) Org Lett 4: 489
14. Liaigre J, Dubreuil D, Pradere J-P, Bouhours J-F (2000) Carbohydr Res 325: 265
15. Overkleeft HS, van Wiltenburg J, Pandit UK (1994) Tetrahedron 50: 4215
16. Davis FA, Reddy GV, Bental M, Deutsch CJ (1994) Synthesis 701
17. Ghosh A, Sieser JE, Caron S, Watson TJN (2002) Chem Commun 1644
18. Lazer ES, Miao CK, Wong H-C, Sorcek R, Spero DM, Watrous JM, Homon CA, Nagel J, Shah A, Guindon Y, Farina PR, Adams J (1994) J Med Chem 37: 913
19. Toujas J-L, Jost E, Vaultier M (1997) Bull Soc Chim Fr 134: 713
20. Sheehan JC, Cruickshank PA, Boshart GL (1961) J Org Chem 26: 2525
21. a) König W, Geiger R (1970) Chem Ber 103: 788;
22. b) Davies JS, Mohammed AK (1981) J Chem Soc, Perkin Trans 1: 2982