Directed approaches to reactive Maillard intermediates: Formation of a novel 3-alkylamino-2-hydroxy-4-hydroxymethyl-2-cyclopenten-1-one ('cypentodine')

Tetrahedron Letters

Volumn 37, Issue 27, 1996, Pages 4667-4670

  Zhang, Xini ^a   Ulrich, Peter ^a  

^a PICOWER INST FOR MEDICAL RESEARCH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPENTENONE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030200004     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00959-8     Document Type: Article

References (14)

1. 1. Hodge, J. E. Advan. Carbohyd. Chem. 1955, 10, 169.
2. 2. Larsen, M. L.; Horder, M.; Mogensen, E. F. New Engl. J. Med. 1990, 323, 1021.
3. 3. Ledl, F.; Schleicher, E. Angew. Chem. Int. Ed. Engl. 1990, 29, 565.
4. 4. Bucala, R.; Cerami, A.; Vlassara, H. Diabetes Rev. 1995, 3, 258.
5. 5. Estendorfer, S.; Ledl, F.; Severin, T. Angew. Chem. Int. Ed. Engl. 1990, 29, 536.
6. 6. a) Nadkarni, D. V.; Sayre, L. M. Chem. Res. Toxicol. 1995, 8, 284.
7. b) Bruenner, B. A.; Jones, A. D.; German, J. B. Chem. Res. Toxicol. 1995, 8, 552.
8. 7. Micheel, F.; Hagemann, G. Chem. Ber. 1959, 92, 2836.
9. 8. Arrick, R. E.; Baker, D. C.; Horton, D. Carbohyd. Res. 1973, 26, 441.
10. 9. Walton, D. J.; McPherson, J. D.; Hvidt, T.; Szarek, W. A. Carbohyd. Res. 1987, 167, 123.
11. 2).
12. 11. Schoetter, C.; Pischetsrieder, M.; Lerche, H.; Severin, T. Tetrahedron Lett. 1994, 35, 7369.
13. +, 186.1130).
14. 13C NMR spectroscopic properties were in accord with literature precedent for the N-butyl analogue of compound 7 (Ref. 11).