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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 7, 1977 - Issue 1
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Original Articles

Synthesis of 2, 5, 5-Trimethylhepta-2, 6-Dien-4-One (Artemisia Ketone): II. Using A Thioacetal Monoxide

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Pages 103-111 | Received 19 Nov 1976, Published online: 01 Apr 2009

References

  • Julia , S. , Ratovelomanana , V. and Huynh , C. 1974 . C.R. Acad. Sci. Paris (C) , 278 : 371
  • Ratovelomanana , V. , Huynh , C. and Julia , S. 1975 . C.R. Acad. Sci. Paris (C). , 280 : 1327
  • Ogura , K. and Tsuchihashi , G. 1971 . Tetrahedron Letters , : 3151 K. Ogura, M. Yamashita, M. Suzuki and G. Tsuchihashi, ibid. 3653(1974); K. Ogura, M. Yamashita, S. Furukawa, M. Suzuki and G. Tsuchihashi, ibid. 2767(1975).
  • Richman , J. E. , Herrmann , J. L. and Schlessinger , R. H. 1973 . Tetrahedron Letters. , : 3267 J. L. Herrmann, J. E. Richman and R. H. Schlessinger, ibid. 3275(1973).
  • Colonge , J. and Dumont , P. 1947 . Bull. Soc. Chim. Fr. , : 38 The first synthesis of artemisia ketone was that of; cf “The Total Synthesis of Natural Products”, J. ApSimon, J. Wiley and Sons, II, p. 40(1973); and literature cited therein; see also J. P. Ruppert and J. D. White, J. Org. Chem. 41, 550(1976) and J-P. Pillot, J. Dunogues and R. Calas, Tetrahedron Letters, 1871(1976) for recent syntheses.
  • Ogura , K. and Tsuchihashi , G. 1972 . Bull. Chem. Soc. Japan , 45 : 2203 There are a number of examples of the asymmetric oxidation of a sulfide to a sulfoxide in which one of a pair of diastereoisomers is produced predominantly. For example see
  • Newkome , G. R. , Robinson , J. M. and Sauer , J. D. 1974 . J. Chem. Soc. Chem. Comm. , : 410 This unexpected-thermal fragmentation has some analogy with the pyrolysis of 2-bis(methylthio)methylpyridine S-oxides
  • Michelot , D. , Linstrumelle , G. and Julia , S. 1974 . J. Chem. Soc. Chem. Comm. , : 10 see also preceding paper.
  • Zalkow , L. H. , Brannon , D. R. and Uecke , J. W. 1964 . J. Org. Chem. , 29 : 2786
  • Huynh , C. , Ratovelomanana , V. and Julia , S. 1975 . C. R. Acad. Sci. Paris (C) , 278 : 1231

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