A convenient synthesis of 4-hydroxy[1-13c]benzoic acid and related ring-labelled phenolic compounds

Synthesis

Volumn , Issue 7, 1998, Pages 1047-1051

  Beyer, Jürgen ^a   Lang Fugmann, Susanne ^a   Mühlbauer, Andrea ^a   Steglich, Wolfgang ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

1,2,4 trihydroxybenzene; 3,4 dihydroxybenzoic acid; 4 hydroxybenzoic acid; 13C labelled aromatic compounds; Tyrosine

Indexed keywords

1,2,4 BENZENETRIOL; 4 HYDROXYBENZOIC ACID; AROMATIC COMPOUND; BENZOIC ACID DERIVATIVE; CARBON 13; PHENOL DERIVATIVE; PROTOCATECHUIC ACID; TYROSINE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; ISOTOPE LABELING; ORGANIC CHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0031854814     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-2109     Document Type: Article

References (25)

1. Gibson, F. Biochem. Soc. Trans. 1973, 1, 317.
2. Olson, R.E.; Rudney, H. Vitam. Horm. 1983, 40, 1.
3. Clarke, C.F.; Williams, W.; Teruya, J.H. J. Biol. Chem. 1991, 266, 16636.
4. Marbois, B.N.; Clarke, C.F. J. Biol. Chem. 1996, 271, 2995.
5. Review: Inouye, H.; Leistner, E. In The Chemistry of Quinonoid Compounds, Patai, S.; Rappoport, Z., Eds.; Wiley: New York, 1988; Vol. 2, p 1294.
6. Zenk, M.H. Z. Naturforsch. (B) 1964, 19, 856.
7. Schmid, H.V.; Zenk, M.H. Tetrahedron Lett. 1971, 4151.
8. Inouye, H.; Ueda, S.; Inoue, K.; Matsumura, H. Phytochemistry 1979, 18, 1301.
9. Heide, L.; Tabata, M. Phytochemistry 1987, 26, 1651.
10. Boehm, R.; Li, S.; Melzer, M.; Heide, L. Phytochemistry 1997, 44, 419.
11. Hanefeld, U.; Floss, H.G.; Laatsch, H. J. Org. Chem. 1994, 59, 3604.
12. Gill, M.; Steglich; W. Prog. Chem. Org. Nat. Prod. 1987, 51, 98.
13. Baldwin, J.E.; Bansal, H.S.; Chondrogianni, J.; Gallagher, P.T.; Taha, A.A.; Taylor, A.; Thaller; V. J. Chem. Res. (S) 1984, 176;
14. J. Chem. Res. (M) 1984, 1815.
15. Viswanatha, V.; Hruby, V.J. J. Org. Chem. 1979, 44, 2892.
16. Musso, H.; Döpp, D. Chem. Ber. 1964, 97, 1147.
17. Musso, H.; Döpp, D.; Kuhles, J. Chem. Ber. 1965, 98, 3937.
18. Müller, R.; Wagener; A.; Schmidt, K.; Leistner; E. Appl. Microbiol. Biotechnol. 1995, 43, 985.
19. Mueller, M.E.; Leete, E. J. Org. Chem. 1981, 46, 3151.
20. Woodward, R.B., private communication to Bergmann, E.D., quoted in Org. React. 1959, 10, 219.
21. Lowenthal, J.; Pepper, J.M. J. Am. Chem. Soc. 1950, 72, 3292.
22. 13C]phenol was obtained by decarboxylation of 5.
23. Matsumoto, M.; Kobayashi, H.; Hotta, Y. J. Org. Chem. 1984, 49, 4740.
24. Brewster, R.Q.; Groening, T. Org. Synth. Coll. Vol. II, 1943, 445.
25. Winkel, C.; Aarts, M.W.MM.; van der Heide, F.R.; Buitenhuis, E. G.; Lugtenburg, J. Recl. Trav. Chim. Pays-Bas 1989, 108, 139.