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Agricultural and Biological Chemistry Volume 52, 1988 - Issue 4
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Organic Chemistry

Transformation of a Marine Toxic Polyether, Okadaic Acid

Yoshiyasu IchikawaLaboratory of Organic Chemistry, Faculty of Agriculture,Nagoya University,Chikusa,Nagoya464,Japan
,
Minoru IsobeLaboratory of Organic Chemistry, Faculty of Agriculture,Nagoya University,Chikusa,Nagoya464,Japan
&
Toshio GotoLaboratory of Organic Chemistry, Faculty of Agriculture,Nagoya University,Chikusa,Nagoya464,Japan
Pages 975-981 | Received 26 Oct 1987, Published online: 06 Jun 2016

References and Notes

  • K. Tachibana, P. J. Scheuer, Y. Tsukitani, H. Kikuchi, D. V. Engen, J. Clardy, Y. Gopichand and F. Schmitz, J. Am. Chem. Soc., 103, 2469 (1981).
  • M. Murata, M. Shimatani, H. Sugitani, Y. Oshima and T. Yasumoto, Bull. Japan. Soc. Sci. Fish., 48, 549 (1982); T. Yasumoto, M. Murata, Y. Oshima, M. Sano, G. K. Matsumoto and J. Clardy, Tetrahedron, 41, 1019 (1985).
  • M. Isobe, Y. Ichikawa and T. Goto, Tetrahedron Lett., 27, 963 (1986).
  • T. W. Greene, “Protective Groups in Organic Synthesis,” John Weily & Sons, New York, 1981.
  • The resulting okadaic acid showed a partially different 1H NMR spectrum from that of the starting okadaic acid. Namely, the resulting product did not show the peak at δ 5.78 ppm (1H, br. s), which was assigned to be the proton of either carboxylic acid or the hydroxy groups. Some impurities seem to have prevented this peak from apprearing in this region.
  • This okadaic acid specimen showed the peak at δ 5.78 ppm.
  • a) M. Isobe, Y. Ichikawa,- H. Masaki and T. Goto, Tetrahedron Lett., 25, 3607 (1984); b) M. Isobe, Y. Ichikawa, D. Bai and T. Goto, ibid., 26, 5199 (1985); c) M. Isobe, Y. Ichikawa and T. Goto, ibid., 26, 5203 (1985); d) Y. Ichikawa, M. Isobe, D. Bai and T. Goto, Tetrahedron, 43, 4737 (1987); e) Y. Ichikawa, M. Isobe and T. Goto, ibid, 43, 4749 (1987); f) Y. Ichikawa, M. Isobe, H. Masaki and T. Goto, ibid., 43, 4759 (1987); g) M. Isobe, Y. Ichikawa, D. Bai, H. Masaki and T. Goto, ibid., 43, 4767 (1987).
  • M. Cherest, H. Felkin and N. Prudent, Tetrahedron Lett., 1968, 2199; T. A. Nguen and U. Eisenstein, Nouv. J. Chim., 1, 61 (1977).
  • K. Tachibana, Ph.D. Dissertation, University of Hawaii, Honolulu, U.S.A., 1980.
  • Y. Ichikawa, M. Isobe and T. Goto, Tetrahedron Lett., 25, 5049 (1984).
  • 1H NMR spectra of the two samples of the acetonide tribenzyl (via Schemes I and II) were identical.
  • M. Miyashita, A. Yoshikoshi and P. A. Grieco, J. Org. Chem., 42, 3772 (1977).
  • L. F. Fieser and M. Fieser, “Reagents for Organic Synthesis,” John Weily & Sons, New York, 1967, p. 191.

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