Reaction of vanilmandelic acid and 4-Hydroxybenzyl alcohol derivatives with L-ascorbic acid

Tetrahedron

Volumn 53, Issue 20, 1997, Pages 6971-6976

  Preobrazhenskaya, M N ^a   Rozhkov, I I ^a   Lazhko, E I ^a   Yudina, L N ^a   Korolev, A M ^a  

^a GAUSE INSTITUTE OF NEW ANTIBIOTICS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

2 FUROIC ACID DERIVATIVE; CYCLOPENTENONE DERIVATIVE;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; IN VITRO STUDY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030920355     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00396-7     Document Type: Article

References (14)

1. Preobrazhenskaya, M.; Bukhman, V.; Korolev, A.; Efimov, S. Pharm. Ther., 1993, 60, 301.
2. Poss, A.; Belter R. J. Org. Chem., 1988, 53, 1535.
3. Alexandrova, L.; Korolev, A.; Preobrazhenskaya, M. Food Chem., 1992, 45, 61.
4. Hasegawa, S.; Hirose, Y., Erdtman, H. Phytochemistry, 1988, 27, 273.
5. Hasegawa, S.; Koynagi, H.; Hirose, Y. Phytochemisiry, 1989, 29, 261.
6. RS-Vanilmandelic (2-hydroxy-4-methoxymandelic acid) (4a) was purchased from Merck. Esters 4b,c can be easily obtained by the incubation of 4a in the corresponding alcohol even in the presence of water.
7. We could not find 13 among minor products of this reaction.
8. 2, but no characteristics were given.
9. Preobrazhenskaya, M.; Lazhko, E.; Korolev, A.; Reznikova, M.I.; Rozhkov, I.I. Tetrahedron Asymmetry, 1996, 7, 461.
10. NMR data for minor components 21a,c were not obtained because of their low content.
11. Under the atmosphere of argon the yield of 10 did not increase.
12. 2-Furancarboxylic acid can also be obtained from 1 and 4c under similar conditions.
13. M.p 133-134°. The Merck Index 9th Ed. Merck & Co. Inc. Rahway, N.J. USA 1976. p. 555.
14. The reaction was carried out in the argon atmosphere.