Synthesis of conformationally locked versions of puromycin analogues

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

doi:10.1021/jo8016132

Synthesis of conformationally locked versions of puromycin analogues

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

Research output: Contribution to journal › Article › peer-review

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 language	English
Pages (from-to)	9435-9438
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	73
Issue number	23
DOIs	https://doi.org/10.1021/jo8016132
Publication status	Published - 2008 Dec 5
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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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.",

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T1 - Synthesis of conformationally locked versions of puromycin analogues

AU - Saneyoshi, Hisao

AU - Michel, Benoît Y.

AU - Choi, Yongseok

AU - Strazewski, Peter

AU - Marquez, Victor E.

PY - 2008/12/5

Y1 - 2008/12/5

N2 - (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.

AB - (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.

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Synthesis of conformationally locked versions of puromycin analogues

Abstract

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