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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 3, 1973 - Issue 1
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Original Articles

Stereoselective Total Synthesis of Sesquiterpenoids: (-)-Ylangocamphor, (-)-Ylangoborneol and (-)-Ylangoisoborneol

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Pages 39-43 | Received 11 Nov 1972, Published online: 06 Dec 2006

References

  • 1970–72 . Fellow of the Alfred P. Sloan Foundation
  • National Research Council of Canada Postdoctoral Fellow
  • Kolbe-Haugwitz , M. and Westfelt , L. 1970 . Acta. Chem. Scand. , 24 : 1623
  • Piers , E. , Britton , R. W. , Keziere , R. J. and Smillie , R. D. 1971 . Can. J. Chem. , 49 : 2620
  • Hodgson , G. L. , MacSweeney , D. F. and Money , T. 1972 . Tetrahedron Letters , : 3683 An elegant total synthesis of racemic ylangocamphor has been recorded:
  • Hikino , H. , Kohama , T. and Takemoto , T. 1969 . Tetrahedron , 25 : 1037 Cf., and references cited therein
  • Walker , D. and Hiebert , J. D. 1967 . Chem. Rev. , 67 : 153
  • House , H. O. , Respess , W. L. and Whitesides , G. M. 1968 . J. Org. Chem. , 33 : 949
  • Piers , E. , Phillips-Johnson , W. M. and Berger; , C. 1972 . Tetrahedron Letters , : 2915 Cf., and references cited therein
  • Tanabe , M. and Crow , D. F. 1969 . Chem. Commun. , : 1498 and references cited therein
  • Use of dimethylsulfoxide or sulfolane as solvent afforded mixtures of 14 and 15 containing considerably less of the desired former compound
  • This chromatography was carried out under a positive pressure (nitrogen), using Camag Kieselgel for TLC (without binder) and 98:2 petroleum ether (65–110°)-ether as eluting solvent. The ratio of compound to silica gel was 1:100

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