An unexpected oxidative decarboxylation reaction of frenolicin-B

Tetrahedron Letters

Volumn 38, Issue 3, 1997, Pages 305-308

  Van Arnum, Susan D ^a   Stepsus, Nancy ^a   Carpenter, Barry K ^b  

^a HOFFMANN LA ROCHE INC   (United States)

^b Department of Population Medicine and Diagnostic Sciences   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,4 NAPHTHOQUINONE DERIVATIVE; FRENOLICIN B; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; DECARBOXYLATION; DRUG OXIDATION; ENTHALPY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; THEORY; ULTRAVIOLET SPECTROPHOTOMETRY;

EID: 0031031178     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02339-8     Document Type: Article

References (10)

1. Current Address: Synthesis Development, Hoffmann-La Roche, Inc., Florence, SC 29502
2. Wells, J. Pharmaceutical Preformulation: The Physicochemical Properties of Drug Substances; Halsted Press, New York, 1988.
3. Iwai, Yuzuru; Kora, Akiko; Takahashi, Yoko; Hayashi, Takako; Awaya, Juichi; Masuma, Rokurou; Oiwa, Ruiko; Omura, Satoshi. J. Antibiot. 1978, 31, 959.
4. Lucarini, M.; Pedulli, G.F.; Cipollone, M. J. Org. Chem. 1994, 59, 5063.
5. a. Arnett, E.M.; Flowers, R.A. Chem.Soc. Rev. 1993, 9.
6. b. Mahoney, L.R.; Ferris, F.C.; DaRooge, M.A. J. Am. Chem. Soc. 1969, 91, 3883.
7. Wagner, D.D. M.; Lusztyk, E.; Pagé, D.; Ingold, K.U.; Mulder, P.; Laarhoven, L.J.J.; Aldrich, H.S. J. Am. Chem. Soc. 1995, 117, 8737.
8. -1 (H-bonded C=O).
9. Interestingly, no reaction was observed under similar conditions when the decomposition was conducted in acetonitrile.
10. 4-methanol at reflux for one day. No H-D exchange was observed at position 5. This observation is consistent with the proposed mechanism. The authors are grateful for the referee's suggestion.