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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 27, 1997 - Issue 24
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Original Articles

A Facile and Practical Procedure for the Synthesis of 8-Hydroxy-4-oxochroman Derivatives

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Pages 4245-4253 | Received 09 Apr 1997, Published online: 22 Aug 2006

REFERENCES AND NOTES

  • Part of the study was reported previously: (a) Yasunaga T. Kimura T. Naito R. Tsukamoto S. Wanibuchi F. Yamaguchi T. Mase T. AFMC International Medicinal Chemistry Symposium Tokyo 1995 P1M067
  • Yasunaga , T. , Naito , R. , Kontani , T. , Tsukamoto , S. , Nomura , T. , Yamaguchi , T. and Mase , T. 1997 . J. Med. Chem. , 40 : 1252
  • For example, see: (a) Bramwell P. S. Fitton A. O. J. Chem. Soc. 1965 3882
  • Anderson , W. K. and La Voie , E. J. 1973 . J. Org. Chem. , 38 : 3832
  • René , L. and Royer , R. 1975 . Eur. J. Med. Chem. - Chim. Ther. , 10 : 72
  • Kawamura , K. , Ohta , T. and Otani , G. 1990 . Chem. Pharm. Bull. , 38 : 2088
  • Canan Koch , S. S. and Chamberlin , A. R. 1989 . Synth. Commun. , 19 : 829
  • Technical grade m-CPBA (TCI, 70% purity) used contained up to 13% of water. Our private assessment shows that the water content of commercial m-CPBA ranges 0.09–18% and varies with the supplier and the lot. Anhydrous m-CPBA was purchased in bulk from Sanken Kako Corp.
  • Available from Aldrich. For the earlier applications of persulfate complex, see: Kennedy R. J. Stock A. M. J. Org. Chem. 1960 25 1901
  • McKillop , A. and Tarbin , J. A. 1987 . Tetrahedron , 43 : 1753
  • Brougham , P. , Cooper , M. S. , Cummerson , D. A. , Heaney , H. and Thompson , N. 1987 . Synthesis , : 1015
  • This was assumed to be a macrocyclic dimer (below): MS (EI) m/z, 55, 364, 237, 182; mp 238°C.

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