Synthesis of 1,2,3,4-tetrahydroxybenzene from D-glucose: Exploiting myo- inositol as a precursor to aromatic chemicals [11]

Journal of the American Chemical Society

Volumn 121, Issue 15, 1999, Pages 3799-3800

  Hansen, Chad A ^a   Dean, Amy B ^a   Draths, K M ^a   Frost, J W ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC COMPOUND; BENZENE DERIVATIVE; GLUCOSE; LOW DENSITY LIPOPROTEIN;

CYCLIZATION; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME SYNTHESIS; GLUCOSE TRANSPORT; HYDROLYSIS; LETTER; OXIDATIVE PHOSPHORYLATION;

EID: 0033594427     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9840293     Document Type: Letter

References (24)

1. (a) Vischer, E. B. J. Chem. Soc. 1953, 815.
2. (b) Baker, W.; McOmie, J. F. W.; Miles, D. J. Chem. Soc. 1953, 820.
3. (c) Baker, W.; Raistrick, H. J. Chem. Soc. 1941, 670.
4. (a) Ingold, K. U.; Bowry, V. W.; Stocker, R.; Walling, C. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 45.
5. (b) Stocker, R.; Bowry, V. W.; Frei, B. Proc. Natl. Acad. Sci. U.S.A. 1991, 88, 1646.
6. (c) Steinberg, D. Circulation 1991, 84, 1420.
7. (a) Honda, G.; Koezuka, Y.; Tabata, M. Chem. Pharm. Bull. 1988, 36, 3153.
8. (b) Tomar, S. S.; Saxena, V. S. Agric. Biol. Chem. 1986, 50, 2115.
9. Postma, P. W.; Lengeler, J. W.; Jacobson, G. R. In Escherichia coli and Salmonella, 2nd ed.; Neidhardt, F. C., Curtiss, R., III, Ingraham, J. L., Lin, E. C. C., Low, K. B., Magasanik, B., Reznikoff, W. S., Riley, M., Schaechter, M., Umbarger, H. E., Eds.; ASM: Washington, 1996; Vol. I, p 1149.
10. Dean-Johnson, M.; Henry, S. A. J. Biol. Chem. 1989, 264, 1274.
11. McAllister, G.; Whiling, P.; Hammond, E. A.; Knowles, M. R.; Atack, J. R.; Bailey, F. J.; Maigetter, R.; Ragan, C. I. Biochem. J. 1992, 284, 749.
12. Yoshida, K.-I.; Aoyama, D.; Ishio, I.; Shibayama, T.; Fujita, Y. J. Bacteriol. 1997, 179, 4591.
13. Posternak, T. Biochem. Prep. 1952, 2, 57.
14. (a) Posternak, T. The Cyclitols; Holden-Day: San Fransisco, 1965; Chapter 8.
15. (b) Angyal, S. J.; Range, D.; Defaye, J.; Gadelle, A. Carbohydr. Res. 1979, 76, 121.
16. (a) Leston, G. In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed.; Kroschwitz, J. I., Howe-Grant, M., Eds.; Wiley: New York, 1996; Vol. 19, p 778.
17. (b) Einhorn, A.; Cobliner, J.; Pfeiffer, H. Ber. Dtsch. Chem. Ges. 1904, 37, 110.
18. Matsumoto, M.; Kobayashi, H.; Hotta, Y. J. Org. Chem. 1985, 50, 1766.
19. Kolonits, P.; Major, Á.; Nógrádi, M. Acta Chim. Hung. 1983, 113, 367.
20. (a) Keinan, E.; Eren, D. J. Org. Chem. 1987, 52, 3872.
21. (b) Syper, L.; Kloc, K.; Mlochowski, J. Tetrahedron 1980, 36, 123.
22. (c) Sugihara, H.; Watanabe, M.; Kawamatsu, Y.; Morimoto, H. Liebigs Ann. Chem. 1972, 763, 109.
23. (d) For an overview of earlier syntheses, see: Mayer, H.; Isler, O. Methods Enzymol. 1971, 18, 182.
24. Trost, B. M. In Green Chemistry; Anastas, P. T., Williamson, T. C., Eds.; Oxford: New York, 1998; Chapter 6.