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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 3
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Original Articles

A Biogenetic-Type Synthesis of Cannabifuran and Dehydrocannabifuran

, &
Pages 203-207 | Published online: 05 Dec 2006

References

  • Jorapur , V. S. , Khalil , Z. H. , Duffley , R. P. and Razdan , R. K. 1982 . Chemical Letters , : 299 Paper 31 in the Hashish Series. For paper 30, see
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  • Scannel , R. T. and Stevenson , R. 1983 . J. Chem. Res. (S) , : 36 We are grateful to Professor Stevenson for giving us the preprint of their paper and providing us with their samples of cannabifuran and dehydrocannabifuran for comparison purposes
  • Novak , J. and Salemink , C. A. 1983 . Tetrahedron Letters , 24 : 101
  • Uliss , D. , Razdan , R. K. and Dalzell , H. C. 1974 . J. Am. Chem. Soc. , 96 : 7372 and the references therein
  • The yield is calculated on the basis of recovered 1a.
  • This incomplete reduction may be attributed to the strong bonding of the aromatic ring with the active sites of platinum so that the reduction product cannot be desorbed.9 When platinum oxide was replaced by palladium/carbon, which binds less strongly to the aromatic ring, the hydrogenation of the double bond was complete within a short time (3h). The difference in the catalytic activity of palladium and platinum catalysts towards the hydrogenation of 5a and 5b is reminiscent of the reduction of phenyl-substituted ethylenes.9b
  • Freifelder , M. 1971 . Practical Catalytic Hydrogenation: Techniques and Applications , 127 – 128 . New York , N. Y. : Wiley-Interscience .
  • Yurashevskii , N. K. 1938 . J. Gen. Chem. USSR , 8 : 438 Chem. Abstr., 32, 7908 (1938)
  • Austin , D. J. and Brown , S. A. 1973 . Phytochem. , 12 : 1657 and the references therein
  • Grundon , M. F. and Jones , K. J. 1971 . Chem. Commun. , : 1311 A. C. Colonna and E. G. Gros, Phytochem., 10, 1515 (1971)
  • Poulose , A. J. and Croteau , R. 1978 . Arch. Biochem. Biophy. , 187 : 307
  • Mechoulam , R. 1970 . Science , 168 : 159 A. Shani and R. Mechoulam, Tetrahedron, 30, 2437 (1974)

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