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Original Articles

Determination of Absolute Stereochemistry at Carbinol Stereocenters of Tetrahydrofuranic Acetogenins by the Advanced Mosher Ester Method

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Pages 117-121 | Received 01 Jul 1994, Published online: 04 Oct 2006

References

  • Rupprecht , J. K. , Hui , Y. H. and McLaughlin , J. L. 1990 . Annonaceous Acetogenins: a Review . Journal of Natural Products , 53 : 237 – 278 . X. -P. Fang, M. J. Rieser, Z. -M. Gu, G. -X. Zhao and J. L. McLaughlin, (1993) Annonaceous Acetogenins: an Updated Review. Phytochemical Analysis, 4, 27–48
  • Hoye , T. R. and Suhadolnik , J. C. 1987 . On the Stereochemistry of the Bistetrahydrofuranyl Moiety of Uvaricin: Proton Chemical Shifts Can Play a Crucial Role in Complex Structure Determination . Journal of the American Chemical Society , 109 : 4402 – 4403 .
  • Born , L. , Lieb , F. , Lorentzen , J. P. , Moeschler , H. , Nonfon , M. , Sollner , R. and Wendisch , D. 1990 . The Relative Configuration of Acetogenins Isolated from Annona squamosa,: Annonin I (Squamocin) and Annonin VI . Planta Medica , 56 : 312 – 316 .
  • Rieser , M. J. , Hui , Y. -H. , Rupprecht , J. K. , Kozlowski , J. F. , Wood , K. V. , Mclaughlin , J. L. , Hanson , P. R. , Zhuang , Z. and Hoye , T. R. 1992 . Determination of Absolute Configuration of Stereogenic Carbinol Centers in Annonaceous Acetogenins by 1H- and 19F-NMR Analysis of Mosher Ester Derivatives . Journal of the American Chemical Society , 114 : 10203 – 10213 .
  • Gale , J. B. , J. , -Yu G. , Khare , A. , Hu , X. E. , Ho , D. K. and Cassady , J. M. 1993 . Stereochemistry of Mono-tetrahydrofuranyl Moiety in Cytotoxic Polyketides. Part B: Application of Proton Chemical Shift Patterns . Tetrahedron Letters , 34 : 5851 – 5854 .
  • Sahai , M. , Singh , S. , Singh , M. , Gupta , Y. K. , Asaki , H. , Araya , H. , Hara , N. , Eguchi , T. , Kakainuma , K. and Fujimoto , Y. 1994 . Annonaceous Acetogenins from the Seeds of Annona squamosa., Adjacent Bis-tetrahydrofuranic Acetogenins . Chemical & Pharmaceutical Bulletin , in press
  • Fujimoto , Y. , Murasaki , C. , Shimada , H. , Nishioka , S. , Kakinuma , K. , Singh , S. , Singh , M. , Gupta , Y. K. and Sahai , M. 1994 . Annonaceous Acetogenins from the Seeds of Annona squamosa., Non-adjacent Bistetrahydrofuranic Acetogenins . Chemical & Pharmaceutical Bulletin , in press
  • Shimada , H. , Nishioka , S. , Sahai , M. and Fujimoto , Y. 1994 . Absolute Stereochemistry of Non-adjacent Bis-tetrahydrofuranic Acetogenins . Tetrahedron Letters , in press
  • Fang , X. -P. , Gu , Z. -M. , Rieser , M. J. , Hui , Y. -H. , McLaughlin , J. L. , Nonfon , M. , Lieb , F. , Moeschler , H. -F. and Wendisch , D. 1993 . Structural Revision of Some Non-adjacent Bis-tetrahydrofuran Annonaceous Acetogenins . Journal of Natural Products , 56 : 1095 – 1100 . For example, the relative stereochemistry of the non-adjacent bis-tetrahydrofuran moiety of squamostatin-A is reported in
  • Ohtani , I. , Kusumi , T. , Kashman , Y. and Kakisawa , H. 1991 . High-Field FT NMR Application of Mosher's Method. The Absolute Configurations of Marine Terpenoids . Journal of American Chemical Society , 113 : 4092 – 4096 .
  • Fujimoto , Y. , Eguchi , T. , Kakinuma , K. , Ikekawa , N. , Sahai , M. and Gupta , Y. K. 1988 . Squamocin, a New Cytotoxic Bis-tetrahydrofuran Containing Acetogenin from Annona squamosa . Chemical & Pharmaceutical Bulletin , 36 : 4802 – 4806 .
  • Fujimoto , Y. , Murasaki , C. , Kakinuma , K. , Eguchi , T. , Ikekawa , N. , Furuya , M. , Hirayama , K. , Ikekawa , T. , Sahai , M. , Gupta , Y. K. and Ray , A. B. 1990 . Squamostatin-A: Unprecedented Bis-tetrahydrofuran Acetogenin from Annona squamosa . Tetrahedron Letters , 31 : 535 – 538 .
  • Cortes , D. , Myint , S. H. and Hocquemiller , R. 1991 . Molvizarin and Motrilin: two Novel Cytotoxic Bis-tetrahydrofuranic γ-Lactone Acetogenins from Annona cherimolia . Tetrahedron , 47 : 8195 – 8202 .

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