Synthesis of Arylglyoxylic Acids
4443
Stereoselective synthesis of germyl substituted tetrahydrofurans. Chem. Com-
mun. 1997, 2357–2358.
2. Chen, Y. T.; Seto, C. Parallel synthesis of a library of bidentate protein tyr-
osine phosphatase inhibitors based on the a-ketoacid motif. Bioorg. Med.
Chem. Lett. 2004, 12, 3289–3298; (b) Chen, Y. T.; Seto, C. Divalent and tri-
valent a-ketocarboxylic acids as inhibitors of protein tyrosine phosphatases.
J. Med Chem. 2002, 45, 3946–3952.
3. Sun, Y.; Wan, X.; Wang, J.; Meng, Q.; Zhang, H.; Jiang, L.; Zhang, Z. Ru-
catalyzed asymmetric hydrogenation of a-ketoesters with CeCl3 7H2O as addi-
tive. Org. Lett. 2005, 7, 5425–5427; (b) Loupy, A.; Monteux, D. A. Isomannide
and isosorbide as new chiral auxiliaries for the stereoselective synthesis of
tertiary a-hydroxy acids. Tetrahedron 2002, 58, 1541–1549; (c) Tanaka, K.;
Katsurada, M.; Ohno, F.; Shiga, Y.; Oda, M. Practical asymmetric synthesis
of (S)-MA20565, a wide-spectrum agricultural fungiside. J. Org. Chem. 2000,
65, 432–437.
4. For a review, see Cooper, A. J. L.; Ginos, J. Z.; Meister, A. Synthesis and
properties of the a-keto acids. Chem. Rev. 1983, 83, 321–358.
5. Wesssels, M.; Konig, G. M.; Wright, A. D. New 4-methoxybenzoyl deriva-
tives from the ascidian polycarpa aurata. J. Nat. Prod. 2001, 64, 1556–
1558; (b) Tsantrizos, Y. S.; Kope, H. H.; Fortin, J. A.; Ogilvie, K. K. Anti-
fungal antibiotics from Pisolithus tinctorius. Phytochem. 1991, 30, 1113–1118.
6. Bellamy, L. J.; Williams, R. L. The infrared spectra of hydroxypyruvic acid
and related compounds Biochem. J. 1958, 18, 81–84; (b) Oki, M.; Hiroto,
M. Intramolecular hydrogen bonding in a-keto and a-alkoxycarboxylic acids,
III: Comparison of the spectra in the carbonyl region with those in the O–H
stretching region. Bull. Chem. Soc. Jpn. 1961, 34, 374–377.
7. Sekiguchi, O.; Letzel, M. C.; Kuck, D.; Uggerud, E. The unimolecular disso-
ciation of protonated glyoxylic acid: Structure and dynamics of step-by-step
process. Int. J. Mass Spectrum. 2006, 255–256, 177–184.
8. Howe, R.; Rao, B. S.; Heyneker, H. 2,3-Dihydro-2-hydroxybenzo[b]furan-3-
one, the cyclic hemiacetal of 2-hydroxyphenylglyoxal. J. Chem. Soc. 1967,
2510–2514; (b) Nardi, D.; Massarini, E.; Rossi, S.; Degen, L.; Altucci, P.;
Catalano, G.; Varone, G. L. Antiviral compounds (XVI) p-alkylthiophenyl-
glyoxals and their derivatives. Farmaco 1974, 29, 473–481.
9. Sprenger, R. D.; Ruoff, R. M.; Frazer, A. H. Citrinin studies: Hydoxy- and
methoxy-phenylglyoxylic acids. J. Am. Chem. Soc. 1950, 72, 2874–2876.
10. Matsuura, T.; Cahnmann, H. J. Model reactions for the biosynthesis of thyr-
oxine: Structural influence of the side chain in analogs of diiodotyrosine on
their conversion to analogs of thyroxine. J. Am. Chem. Soc. 1959, 81,
871–878; (b) Barnish, I. T.; Cross, P. E.; Danilewicz, J. C.; Dickinson,
R. C.; Stopher, D. A. Promotion of carbohydrate oxidation in the heart by
some phenylglyoxylic acids. J. Med. Chem. 1981, 24, 399–404.
11. Jefford, C. W.; Boschung, A. F.; Bolsman, T. A. B. M.; Moriarty, R. M.;
Melnick, B. Reaction of singlet oxygen with a-ketocarboxylic acids: Oxyda-
tive decarboxylation and peroxyacid formation. J. Am. Chem. Soc. 1976,
94, 1017–1018; (b) Ando, W.; Miyazaki, H.; Akasaka, T. Decarboxylation