Journal
MOLECULES
Volume 15, Issue 6, Pages 3816-3828Publisher
MDPI
DOI: 10.3390/molecules15063816
Keywords
cyclobutanone; oxacarbene; bicyclic nucleosides; isonucleosides; acyclic nucleoside
Funding
- NSERC
- Government of Egypt
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The preparation of two nucleoside analogues are reported. Both syntheses involve a key photochemical ring-expansion of cyclobutanones to an oxacarbene and its subsequent scavenging by 6-chloropurine. The synthesis of a bicyclic (locked) purine starts from a oxabicycloheptanone with a hydroxymethyl pendant. The preparation of an isonucleoside uses a cyclobutanone with an alpha-substituted 6-chloropurine. Irradiation of the latter produces an isonucleoside and acyclic nucleoside analogues.
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