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Synthesis of Conformationally Locked Versions of Puromycin Analogues

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journal contribution
posted on 05.12.2008, 00:00 by Hisao Saneyoshi, Benoît Y. Michel, Yongseok Choi, Peter Strazewski, Victor E. Marquez
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.