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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 38, 2008 - Issue 5
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Original Articles

New Synthesis of 2,2‐Bis(hydroxymethyl) methylenecyclopropane, a Key Intermediate for Antiviral Cyclopropavir

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Pages 697-702 | Received 05 Sep 2007, Published online: 15 Feb 2008

References

  • Zhou , S. , Breitenbach , J. M. , Borysko , K. Z. , Drach , J. C. , Kern , E. R. , Gullen , E. , Cheng , Y.‐C. and Zemlicka , J. 2004 . Synthesis and antiviral activity of (Z)‐ and (E)‐2,2‐[bis(hydroxymethyl)cyclopropylidene]methylpurines and ‐pyrimidines: Second‐generation methylenecyclopropane analogues of nucleosides . J. Med. Chem. , 47 : 566 – 575 .
  • Yan , Z. , Kern , E. R. , Gullen , E. , Cheng , Y.‐C. , Drach , J. C. and Zemlicka , J. 2005 . Nucleotides and pronucleotides of 2,2‐bis(hydroxymethyl)methylenecyclopropane analogues of purine nucleosides: Synthesis and antiviral activity . J. Med. Chem. , 48 : 91 – 99 .
  • Kern , E. R. , Bidanset , D. J. , Hartline , C. B. , Yan , Z. , Zemlicka , J. and Quenelle , D. C. 2004 . Oral activity of a methylenecyclopropane analog, cyclopropavir, in animal models for cytomegalovirus infections . Antimicrob. Agents Chemother. , 48 : 4745 – 4753 .
  • Kern , E. R. , Kushner , N. L. , Hartline , C. B. , Williams‐Azziz , S. L. , Harden , E. A. , Zhou , S. , Zemlicka , J. and Prichard , M. N. 2005 . In vitro activity and mechanism of action of methylenecyclopropane analogs of nucleosides against herpesvirus replication . Antimicrob. Agents Chemother. , 49 : 1039 – 1045 .
  • Dolbier , W. R. Jr. , Akiba , K. , Riemann , J. M. , Harmon , C. A. , Bertrand , M. , Bezaguet , A. and Santelli , M. 1971 . The thermal reorganization of C6H8 hydrocarbons . J. Am. Chem. Soc. , 93 : 3933 – 3940 .
  • Ullman , E. F. 1959 . Mechanism of hydrogenation of unsaturated cyclopropanes . J. Am. Chem. Soc. , 81 : 5386 – 5392 .
  • Joucla , M. , Fouchet , B. , Le Brun , J. and Hamelin , J. 1985 . Reactions de cyclopropanation par double addition de Michael . Tetrahedron Lett. , 26 : 1221 – 1224 .
  • Osborne , N. F. 1980 . The chemistry of 4‐mercaptoazetidin‐2‐ones, part 2: Synthesis of bisnorpenicillins . J. Chem. Soc. Perkin Trans. 1 , : 150 – 155 .
  • Dulayymi , A. R. A. , Dulayymi , J. R. A. , Baird , M. S. , Gerrard , M. E. , Koza , G. , Harkins , S. D. and Roberts , E. 1996 . 1,2,2‐Tribromocyclopropanecarboxylic acid and derivatives—valuable intermediates for four carbon cyclopropane and cyclopropene synthons . Tetrahedron , 52 : 3409 – 3424 .
  • Zhou , S. , Prichard , M. N. and Zemlicka , J. 2007 . Methylene‐2‐ethynylcyclopropanes: synthesis and biological activity of (Z)‐ and (E)‐9‐{[2‐ethynyl‐2‐(hydroXYmethyl)cyclopropylidene]methyl}‐adenine and ‐guanine . Tetrahedron , 63 : 9406 – 9412 .

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