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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 14, 1984 - Issue 2
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Original Articles

Bicyclo[3.3.1]Nonanes as Synthetic Intermediates. Vii.(1) An Intramolecular Alkylation in the Bicyclo[3.3.1]nonan-3-One System by the “fork head” endo-Methanol: An Efficient Route to 4-Protoadamantanone

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Pages 147-154 | Published online: 05 Dec 2006

References

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  • Lenoir , D. , Hall , R. E. and Schleyer , P. V. R. 1974 . J. Am. Chem. Soc. , 96 : 2138
  • Chakrabarti , J. K. , Hotten , T. M. , Sutton , S. and Tupper , D. E. 1976 . J. Med. Chem. , 19 : 967
  • Raber , D. J. and Janks , C. M. 1983 . J. Org. Chem. , 48 : 1101 Hiršl-Starčevic, S. and Majerski,Z., ibid., 1982, 47, 2520; Nordlander, J. E. and Haky, J. E., J. Am. Chem. Soc., 1981, 103, 1518; Chakrabarti, J. K., Hotten, T. M., Rackham, D. M., and Tupper, D. E., J. Chem. Soc. Perkin I, 1976, 1893; Lenoir, D., Chem. Ber., 1973, 106, 78; Idem, ibid., 1973, 106, 2366; Tabushi, I. and Aoyama, Y., J. Org. Chem., 1973, 38, 3447; Lenoir, D., Glaser, R., Mison, P., and Schleyer, P. V. R., J. Org. Chem., 1971, 36, 1821; Cuddy, B. D., Grant, D., and McKervey, M. A., J. Chem. Soc. C, 1971, 3173
  • Majerski , Z. , Šarac-Arneri , R. , Škare , D. and Lončar , B. 1980 . Synthesis , : 74
  • Takaishi , N. , Inamoto , Y. , Aigami , K. , Fujikura , Y. , ōsawa , E. , Kawanisi , M. and Katsushima , T. 1977 . J. Org Chem. , 42 : 2041
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  • Majerski , Z. and Hameršak , Z. 1979 . Org. Synth. , 59 : 147
  • Zalikowski , J. A. , Gilbert , K. E. and Borden , W. T. 1980 . J. Org. Chem. , 45 : 346 and references cited therein
  • Tomioka , H. , Oshima , K. and Nozaki , H. 1982 . Tetrahedron Lett. , : 539
  • Present in the form of a hemiacetal in solid, but in an equilibrium with a ketol in solution as evidenced by its carbonyl-carbon resonance at 212.9 ppm in the 13CNMR spectrum: see also ref. 11.
  • Corey , E. J. and Schmidt , G. 1979 . Tetrahedron Lett. , : 399
  • The PDC oxidation of 2 has been reported to give 3 in 50% yield (see ref. 11). A reduced reaction period and use of three molar amounts of the reagent improved the yield up to 85%.
  • 1HNMR spectra were taken for the 10% solution in CDCl3 with a JEOL JNM-FX-200 spectrometer with TMS as an internal standard. IR spectra were taken with a Hitachi 2:60–30 IR spectrometer. GC-Mass spectra were taken on a Hitachi M-70 mass spectrometer.
  • Momose , T. , Masuda , K. , Kanada , Y. and Muraoka , O. An alternative route to the protoadamahtanone skeleton, comprising the intramolecular alkylation in the ketooxirane as shown below, was also found to occur in an excellent yield to give 1-hydroxy-4-protoada-mantanone unpublished work.
  • A facile conversion of 2-adamantanone into the glycol 2 is known (94% yield): see ref. 11.
  • The filtration through silica gel was found more effective than that through Florisil reported.11)
  • Mehta , G. and Pandey , P. N. 1975 . Synthesis , : 404 The nomenclature is improperly given in ref. 11. Cf.

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