Synthesis of conformationally locked versions of puromycin analogues

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

Research output: Contribution to journalArticle

10 Citations (Scopus)

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
Externally publishedYes

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Puromycin
Carbasugars
Azides
Tyrosine
Esters
1-hydroxybenzotriazole
south 7
bicyclo(3.1.0)hexane

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

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

Synthesis of conformationally locked versions of puromycin analogues. / Saneyoshi, Hisao; Michel, Benoît Y.; Choi, Yongseok; Strazewski, Peter; Marquez, Victor E.

In: Journal of Organic Chemistry, Vol. 73, No. 23, 05.12.2008, p. 9435-9438.

Research output: Contribution to journalArticle

Saneyoshi, H, Michel, BY, Choi, Y, Strazewski, P & Marquez, VE 2008, 'Synthesis of conformationally locked versions of puromycin analogues', Journal of Organic Chemistry, vol. 73, no. 23, pp. 9435-9438. https://doi.org/10.1021/jo8016132
Saneyoshi, Hisao ; Michel, Benoît Y. ; Choi, Yongseok ; Strazewski, Peter ; Marquez, Victor E. / Synthesis of conformationally locked versions of puromycin analogues. In: Journal of Organic Chemistry. 2008 ; Vol. 73, No. 23. pp. 9435-9438.
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