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Agricultural and Biological Chemistry Volume 43, 1979 - Issue 11
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Biological Chemistry

Novel Synthesis of 3-Hydroxy-β-damascone, 3-Hydroxydihydro-β-damascone and β-damascenone

Takeshi KitaharaThe Institute of Physical and Chemical Research, 2-1 Hirosawa, Wako-shi, Saitama351, Japan
,
Yoshikazu TakagiThe Institute of Physical and Chemical Research, 2-1 Hirosawa, Wako-shi, Saitama351, Japan
&
Masanao MatsuiThe Institute of Physical and Chemical Research, 2-1 Hirosawa, Wako-shi, Saitama351, Japan
Pages 2359-2363 | Received 25 Jun 1979, Published online: 09 Sep 2014

References

  • Present address; Department of Agricultural Chemistry, The University of Tokyo, 1-1-1 Yayoi, Bunkyo-ku, 113, Tokyo, Japan.
  • Research Fellow from Central Research Laboratory of T. Hasegawa Co. Ltd.
  • E. Demole, P. Enggist, U. Säuberli, M. Stoll and E. Sz. Kovats, Helv. Chim. Acta, 53, 541 (1970).
  • a) H. Kaneko and M. Harada, Agric. Biol. Chem., 36, 168 (1972). b) T. Fujimori, R. Kasuga, H. Matsushita, H. Kaneko and M. Noguchi, ibid., 40, 303 (1976).
  • S. Shibata, A. Katsuyama and M. Noguchi, ibid., 42, 195 (1978).
  • a) E. Demole and D. Berthet, Helv. Chim. Acta, 54, 681 (1971); 55, 1866 (1972). b) B. Kimland, A. J. Aasen and C. R. Enzell, Acta. Chem. Scand., 26, 2177 (1972).
  • a) G. Ohloff and G. Uhde, Helv. Chim. Acta, 53, 531 (1970). b) K. H. Schulte-Elte, V. Rautenstrauch and G. Ohloff, ibid., 54, 1805 (1971). c) K. H. Schulte-Elte, B. L. Müller and G. Ohloff, ibid., 54, 1899 (1971); 56, 310 (1973). d) V. Rautenstrauch, ibid., 56, 2492 (1973). e) G. Buchi and H. Wuest, ibid., 54, 1767 (1971). f) G. Buchi and J. C. Vederas, J. Am. Chem. Soc. 94, 9128 (1972). g) K. S. Ayyar, R. C. Cookson and D. A. Kagi, J. Chem. Soc. Perkin I, 1975, 1727. h) S. Isoe, S. Katsumura and T. Sakan, Helv. Chim. Acta, 56, 1814 (1973). i) 3-hydroxy-β-damascone; G. Ohloff, V. Rautenstrauch and K. H. Schulte-Elte, Helv. Chim. Acta, 56, 1503 (1973). j) 3-hydroxydihydro-β-damascone; K. Mori, M. Ohki, K. Okada, Y. Takei and M. Matsui, Agric. Biol. Chem., 37, 2907 (1973).
  • S. Danishefsky and T. Kitahara, J. Am. Chem. Soc., 96, 7807 (1974); J. Org. Chem., 40, 538 (1975).
  • a) H. O. House, W. L. Respess and G. M. Whitesides, J. Org. Chem., 31, 3128 (1966). b) G. H. Posner, Org. Reactions, 19, 1 (1972).
  • G. Stork, G. A. Kraus and G. A. Garcia., J. Org. Chem., 39, 3459 (1974).
  • When N-methylanilinomagnesium bromide was used as base, most of the starting ketone was recovered.
  • H. C. Brown and S. Krishnamurthy, J. Am. Chem. Soc., 94, 7159 (1972).
  • Authentic dihydro-β-damascenone (1b) was prepared by reduction of 1a with LiAlH(OBut)3 in quantitative yield, (cf. ref. 7c).

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