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Synthesis of Conformationally Locked Versions of Puromycin Analogues

  1. Author:
    Saneyoshi, H.
    Michel, B. Y.
    Choi, Y.
    Strazewski, P.
    Marquez, V. E.
  2. Author Address

    Saneyoshi, Hisao, Choi, Yongseok, Marquez, Victor E.] NCI, Ctr Canc Res, Med Chem Lab, Frederick, MD 21702 USA. [Michel, Benoit Y.; Strazewski, Peter] Univ Lyon 1, Lab Synth Biomol, Inst Chim & Biochim Mol & Supramol, UMR 5246, F-69622 Villeurbanne, France.
    1. Year: 2008
  1. Journal: Journal of Organic Chemistry
    1. 73
    2. 23
    3. Pages: 9435-9438
  2. Type of Article: Article
  1. Abstract:

    Conformationally locked North and South versions Of puromycin analogues built on a bicyclo[3.1.0]hexane pseudosugar template were synthesized. The final assembly of the products was accomplished by the staudinger-Vilarrasa coupling of the corresponding North (2 and 3) and South (6 and 7) 3'-azidopurine carbanucleosides with the Fmoc-protected 1-hydroxybenzotriazole ester of 4-methoxy-L-tyrosine. North azides 2 and 3 were reported earlier. The 3'-azido intermediates 6 and 7 that are necessary for the synthesis of the South puromycin analogues are described herein for the first time.

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