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 | |
| Publication status | Published - 2008 Dec 5 |
| Externally published | Yes |
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ASJC Scopus subject areas
- Organic Chemistry
Cite this
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 journal › Article
}
TY - JOUR
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.
UR - http://www.scopus.com/inward/record.url?scp=57449087631&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=57449087631&partnerID=8YFLogxK
U2 - 10.1021/jo8016132
DO - 10.1021/jo8016132
M3 - Article
C2 - 18991379
AN - SCOPUS:57449087631
VL - 73
SP - 9435
EP - 9438
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
SN - 0022-3263
IS - 23
ER -