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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2009 - Issue 2
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Original Articles

Acid-Catalyzed E-Ring Expansion and Isomerization of 3-Acetylbetulin: Synthesis of Cytotoxic Anhydrobetulin Saponins

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Pages 213-221 | Received 22 Feb 2009, Published online: 29 Dec 2009

REFERENCES

  • Hayek , E. W. H. ; Jordis , U. ; Moche , W. ; Sauter , F. A bicentennial of betulin . Phytochemistry 1989 , 28 , 2229 – 2242 .
  • O'Connell , M. M. ; Bentley , M. D. ; Campbell , C. S. ; Cole , B. J. W. Betulin and lupeol in bark from four white-barked birches . Phytochemistry 1988 , 27 , 2175 – 2176 .
  • Fuchino , H. ; Konishi , S. ; Satoh , T. ; Yagi , A. ; Saitsu , K. ; Tatsumi , T. ; Tanaka , N. Chemical evaluation of Betula species in Japan, II: Constituents of Betula platyphylla var . japonica. Chem. Pharm. Bull. 1996 , 44 , 1033 – 1038 .
  • Habiyaremye , I. ; Stevanovic-Janezic , T. ; Riedl , B. ; Garneau , F.-X. G. ; Jean , F.-I. Pentacyclic triterpene constituents of yellow birch bark from Quebec . J. Wood Chem. Technol. 2002 , 22 , 83 – 91 .
  • Gauthier , C. ; Legault , J. ; Lebrun , M. ; Dufour , P. ; Pichette , A. Glycosylation of lupane-type triterpenoids as potent in vitro cytotoxic agents. Bioorg. Med. Chem. 2006, 14, 6713–6725.
  • Kolomitsyn , I. V. ; Holy , J. ; Perkins , E. ; Krasutsky , P. A. Analysis and antiproliferative activity of bark extractives of Betula neoalaskana and B. papyrifera. Synthesis of the most active extractive component—betulin 3-caffeate . Nat. Prod. Commun. 2007 , 2 , 17 – 26 .
  • Krasutsky , P. A. Birch bark research and development . Nat. Prod. Rep. 2006 , 23 , 919 – 942 .
  • Sami , A. ; Taru , M. ; Salme , K. ; Jari , Y.-K. Pharmacological properties of the ubiquitous natural product betulin . Eur. J. Pharm. Sci. 2006 , 29 , 1 – 13 .
  • Thibeault , D. ; Gauthier , C. ; Legault , J. ; Bouchard , J. ; Dufour , P. ; Pichette , A. Synthesis and structure–activity relationship study of cytotoxic germanicane- and lupane-type 3β-O-monodesmosidic saponins starting from betulin . Bioorg. Med. Chem. 2007 , 15 , 6144 – 6157 .
  • Gauthier , C. ; Legault , J. ; Lavoie , S. ; Rondeau , S. ; Tremblay , S. ; Pichette , A. Synthesis of two natural betulinic acid saponins containing α-L-rhamnopyranosyl-(1→2)-α-L-arabinopyranose and their analogues . Tetrahedron 2008 , 64 , 7386 – 7399 .
  • Gauthier , C. ; Legault , J. ; Lavoie , S. ; Rondeau , S. ; Tremblay , S. ; Pichette , A. Synthesis and cytotoxicity of bidesmosidic betulin and betulinic acid saponins . J. Nat. Prod. 2009 , 72 ( 1 ), 72 – 81 .
  • Lavoie , S. ; Pichette , A. ; Garneau , F.-X. ; Girard , M. ; Gaudet , D. Synthesis of betulin derivatives with solid supported reagents . Synth. Commun. 2001 , 31 , 1565 – 1571 .
  • Odinokova , L. É. ; Oshitok , G. I. ; Denisenko , V. A. ; Anufriev , V. F. ; Tolkach , A. M. ; Uvarova , N. I. Glycosylation of betulin and its acetates in the presence of cadmium carbonate . Chem. Nat. Compd. 1984 , 20 , 168 – 173 .
  • Odinokova , L. E. ; Denisenko , M. V. ; Denisenko , V. A. ; Uvarova , N. I. Glycosylation of triterpene alcohols of the lupane series . Chem. Nat. Compd. 1988 , 24 , 178 – 183 .
  • Fuchino , H. ; Nozawa , O. ; Tanaka , N. Double bond migration on the 22(17 → 28)abeo-lupane skeleton . Chem. Pharm. Bull. 1994 , 42 , 1745 – 1749 .
  • Flekther , O. B. ; Boreko , E. I. ; Nigmatullina , L. R. ; Pavlova , N. I. ; Medvedeva , N. I. ; Nikolaeva , S. N. ; Ashavina , O. A. ; Savinova , O. V. ; Baltina , L. A. ; Galin , F. Z. ; Tolstikov , G. A. Synthesis and antiviral activity of lupane triterpenoids and their derivatives . Pharm. Chem. J. 2004 , 38 , 355 – 358 .
  • Protiva , J. ; Krecek , V. ; Kreckova , J. ; Klinitova , E. ; Vystrcil , A. Triterpenes, LXVII: The synthesis and the mass spectra of 28,29,30-trinoroleanane derivatives with a double bond in the ring E or D . Collect. Czech. Chem. Commun. 1983 , 48 , 928 – 936 .
  • Ikeda , T. ; Kajimoto , T. ; Kondo , H. ; Wong , C.-H. Design and synthesis of an α-mannosyl terpenoid as selective inhibitor of P-selectin . Bioorg. Med. Chem. Lett. 1997 , 7 , 2485 – 2490 .
  • Vystrcil , A. ; Krecek , V. ; Budesinsky , M. Triterpenes, LXVIII: Elimination reaction of angular hydroxymethyl groups of 20(29)-lupene derivatives . Collect. Czech. Chem. Commun. 1983 , 48 , 1499 – 1507 .
  • Vystrcil , A. ; Krecek , V. ; Protiva , J. ; Budesinsky , M. Triterpenes, XCIII: Anhydrobetulin and its derivatives . Collect. Czech. Chem. Commun. 1991 , 56 , 886 – 904 .
  • Krecek , V. ; Hilgard , S. ; Budesinsky , M. ; Vystrcil , A. Triterpenes, CIV: E-homolupane derivatives substituted in position 17 and 22a: 1H NMR, 13C NMR and IR spectra . Collect. Czech. Chem. Commun. 1995 , 60 , 619 – 635 .
  • O'Brien , J. ; Wilson , I. ; Orton , T. ; Pognan , F. Investigation of the Alamar Blue (resazurin) fluorescent dye for the assessment of mammalian cell cytotoxicity . Eur. J. Biochem. 2000 , 267 , 5421 – 5426 .
  • Kessler , J. H. ; Mullauer , F. B. ; de Roo , G. M. ; Medema , J. P. Broad in vitro efficacy of plant-derived betulinic acid against cell lines derived from the most prevalent human cancer types . Cancer Lett. 2007 , 25 , 132 – 145 .

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