Format:
Online-Ressource
ISSN:
1521-4184
Content:
Abstract: In this study, a series of 2′, 4‐′ or 3′, 4′‐doubly branched carbocyclic nucleosides (11, 12, 19, and 20) were synthesized from simple acyclic ketone derivatives as starting materials. The installation of the 4′‐quaternary carbon needed was carried out using a [3, 3]‐sigmatropic rearrangement. In addition, the introduction of a methyl group in the 2′‐ or 3′‐position was accomplished by either Grignard reaction or Horner‐Wadsworth‐Emmons reaction with triethyl‐2‐phosphonopropionate, respectively. Bis‐vinyl was successfully cyclized using a Grubbs' catalyst II. The natural bases (adenine, cytosine) were coupled efficiently using a Pd (0) catalyst. Although all the synthesized compounds were assayed against several viruses, only the cytosine analogue 20 showed moderate antiviral activity against the human cytomegalovirus.
In:
volume:337
In:
number:8
In:
year:2004
In:
pages:457-463
In:
extent:7
In:
Archiv der Pharmazie, Weinheim : Wiley-VCH, 1822-, 337, Heft 8 (2004), 457-463 (gesamt 7), 1521-4184
Language:
English
DOI:
10.1002/ardp.200400875
URN:
urn:nbn:de:101:1-2023100804350529601013
URL:
https://doi.org/10.1002/ardp.200400875
URL:
https://nbn-resolving.org/urn:nbn:de:101:1-2023100804350529601013
URL:
https://d-nb.info/1305311221/34
URL:
https://doi.org/10.1002/ardp.200400875
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