Synthesis of conformationally locked versions of puromycin analogues

Hisao Saneyoshi, Benoît Y. Michel, Yongseok Choi, Peter Strazewski, Victor E. Marquez

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Abstract

(Chemical Equation Presented) 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.

Original languageEnglish
Pages (from-to)9435-9438
Number of pages4
JournalJournal of Organic Chemistry
Volume73
Issue number23
DOIs
Publication statusPublished - 2008 Dec 5

ASJC Scopus subject areas

  • Organic Chemistry

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    Saneyoshi, H., Michel, B. Y., Choi, Y., Strazewski, P., & Marquez, V. E. (2008). Synthesis of conformationally locked versions of puromycin analogues. Journal of Organic Chemistry, 73(23), 9435-9438. https://doi.org/10.1021/jo8016132