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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 16, 1986 - Issue 4
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Original Articles

Total Synthesis of (±)-Epiisocomenes VIA Hydrogenation of “Chatterjee's Ketone”

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Pages 393-399 | Published online: 05 Dec 2006

References

  • Sloan , Alfred P. Fellow of the, Foundation, 1981–85; Research Career Development Award Recipient, 1984–89 (NIH, AI-00564)
  • Kaneda , M. , Takahashi , R. , Iitaka , Y. and Shibata , S. 1972 . Tetrahedron Lett. , : 4609
  • Zalkow , L. H. , Harris , R. N. , van Deveer , D. and Bertrand , J. A. 1977 . J. Chem. Soc. Chem. Commun. , 456 Isolation of isocomene, Bohlman, F.; Le Van, N.; Pickardt, J. Chem. Berr., 1977, 110, 3777. Isolation of β-isocomene; Bohlman, F.; Le Van, F.; Pham, T. V. C.; Jakupovic, J.; Schuster, A.; Zabel, V.; Watson, W. H. Phytochemistry, 1979, 18, 1831. For isolation and structure elucidation of other triquinanes, see the references listed in: L. A. Paquette, Recent Synthetic Developments in Polyquinane Chemistry, Topics in Current Chemistry, F. L. Boschke, ed., vol. 119, Verlag (1984)
  • Chatterjee , S. 1979 . J. Chem. Soc. Chem. Commun. , : 620
  • Oppolzer , W. , Battig , K. and Hudlicky , T. 1981 . Tetrahedron , 37 : 4359 Isocomene total syntheses:
  • Oppolzer , W. , Battig , K. and Hudlicky , T. 1979 . Helv. Chim. Acta , 62 : 1493
  • Paquette , L. A. and Han , Y. K. 1979 . J. Org. Chem. , 44 : 4014 J. Am. Chem. Soc. 103, 1835 (1981);
  • Pirrung , M. C. 1979 . J. Am. Chem. Soc. , 101 : 7130 J. Am. Chem. Soc. 103, 82 (1981);
  • Dauben , W. G. and Walker , D. M. 1981 . J. Org. Chem. , 46 : 1103
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  • Wenkert , E. and Arrhenius , S. 1983 . J. Am. Chem. Soc. , 105 : 2030
  • Ranu , B. C. , Kavka , M. , Higgs , L. A. and Hudlicky , T. 1984 . Tetrahedron Lett. , 2447
  • Short , R. P. , Ranu , B. C. , Revol , J. M. and Hudlicky , T. 1983 . J. Org. Chem. , 48 : 4453
  • Tobe , Y. , Yamashita , T. , Kakiochi , K. and Odaira , Y. 1985 . J. Chem. Soc. Chem. Commun. , : 898
  • Short , R. P. 1984 . M.S. thesis Virginia Polytechnic Institute and State University . Preparation of the ethyl ester of 5:, Kwart, L. D.; Tiedje, M.; Short, R. P.; Frazier, J. O.; Hudlicky, T.; J. Org. Chem., in preparation
  • Hudlicky , T. , Kutchan , M. and Naqvi , S. 1984 . Org. Reactions , 33 : 247 For a description of this methodology, see, ref. 5h.
  • All compounds were fully characterized by IR, 1H-NMR, 13C-NMR, and mass spectrometry
  • The paper by s. Chatterjee gives only a few details concerning the hydrogenation. Given the unpredictability of catalytic reactions in general, these conditions represented the best estimate of the ones reported

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