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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 26, 1996 - Issue 19
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Original Articles

Asymmetric Friedel - Crafts Reaction: An Application to the Synthesis of an Etodolac Analogue

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Pages 3671-3676 | Received 14 Apr 1996, Published online: 21 Aug 2006

References

  • Etodolac can be purchased from Wyeth-Ayerst Laboratories Inc. as LodineR
  • Demerson , C. A. , Humber , L. G. , Philipp , A. H. and Martel , R. R. 1976 . J. Med. Chem. , 19 : 391 – 395 .
  • Demerson , C. A. , Humber , L. G. and Dobson , T. A. 1983 . J. Med. Chem. , 26 : 1778 – 1780 .
  • Bigi , F. 1993 . Tetrahedron asymmetry , 4 : 2411
  • Waldmann , H. , Schimidt , G. , Jansen , M. and Geb , J. 1994 . Tetrahedron , 50 : 1965 – 1972 . A chiral version for the Picted-Spengler reaction, “aza analogous process” was recently reported
  • Oppolzer , W. 1987 . Tetrahedron , 43 : 1969
  • Vasconcellos , M. L. L. A. , Dángelo , J. , Desmaelle , D. , Costa , P. R. R. and Potin , D. 1991 . Tetrahedron Asymmetry , 2 : 353 Colaborative work with the research group directed by Dr Jean d'Angelo. (Université Paris sud) Work supported by CNPq-CNRS 910237/94—9 (NV)
  • Taber , D. F. , Decker , P. B. and Michael , D. G. 1987 . J. Am. Chem. Soc. , 109 : 7488
  • Corey , E. J. and Enslesy , H. F. 1975 . J. Am. Chem. Soc. , 97 : 6908
  • d'Angelo , J. and Madalluno , J. 1986 . J. Am. Chem. Soc. , 108 : 8112 and cited references
  • Stereoselectivities were determined by HPLC (6f) and quantitative 13C NMR (6a-6f) HPLC conditions: (analysis of 7 and 6f) Mobile phase: 90% MeOH 10% H2O, flowrate: 1.0 ML/min, detector: UV 275 nm, 0.2 AUFS, column: 75mm—4.6 cm, packing: ultrasphere C18, 3μ, retention time of 6f= 6.83min.; 7= 4.26min. The compounds 6f and 7 have purity above 95%
  • Smith , W. B. 1994 . Mag. Reson. Chem. , 32 : 316
  • Laihia , K. 1992 . Mag. Reson. Chem. , 30 : 754

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