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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 11, 1981 - Issue 6
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Original Articles

Dehydrogenation of Triterpenoid Alcohols in Alkali Melt. A Short Synthesis of the So-Called Jasminol

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Pages 489-492 | Published online: 05 Dec 2006

References

  • Weedon , B. C. L. 1973 . “ Alkali Fusion and some Related Processes ” . In Elucidation of Organic Structures by Physical and Chemical Methods , 2nd ed. , Edited by: Bentley , K. W. and Kirby , G. W. 325 New York, NY : Wiley-Interscience . Part II, See also H. Henecka in Houben-Weyl, Methoden der organischen Chemie (ed. E. Müller), Vol. 8, p. 404. Georg Thieme Verlag, Stuttgart 1952
  • Isolated yields are shown, and are calculated after deduction of unreacted starting material. Products were identified by 1H and 13C NMR (cf. ref. 11 and 12) and mass spectra, and by direct comparison with authentic materials
  • Significantly longer reaction times than shown give ring A cleavage products (dicarboxylic acids)
  • Osman , A. M. , Younes , M. E.-G. and Mokhtar , A. 1975 . Indian J. Chem. , 13 : 193 D. H. R. Barton, D. J. Lester and S. V. Ley, Chem. Commun. 130 (1978)
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  • A direct comparison of our 9 with the natural material has not been possible
  • Ruzicka , L. and Heineman , S. D. 1940 . Helv. Chim. Acta , 23 : 1512 M. Marx, J. Leclercq, E. Tursch and C. Djerassi, J. Org. Chem. 32, 3151 (1967)
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