118237-82-4Relevant academic research and scientific papers
Synthesis of (+/-)-2',3'-Didehydro-2',3'-dideoxy Nucleosides via a Modified Prins Reaction and Palladium(0) Catalysed Coupling
Saville-Stones, Elizabeth A.,Lindell, Stephen D.,Jennings, Neil S.,Head, John C.,Ford, Mark J.
, p. 2603 - 2604 (1991)
Cyclopentenyl allylic acetates have been prepared in diastereoisomerically enriched form by modification of the Prins reaction.Palladium(0) catalysed coupling between these allylic acetates and a heteroaromatic base provides a highly convergent and direct route for synthesising carbocyclic 2',3'-didehydro-2',3'-dideoxy nucleosides.The method is exemplified by the coupling reaction with adenine which yields (+/-)-2',3'-didehydro-2',3'-dideoxyaristeromycin 5'-O-acetate 22 in 50percent yield.This has been converted in two steps into (+/-)-aristeromycin triacetate 5.
A Novel, One-Pot Ring Expansion of Cyclobutanones. Syntheses of Carbovir and Aristeromycin
Brown, Brian,Hegedus, Louis S.
, p. 1865 - 1872 (2007/10/03)
A novel, one-pot ring-expansion procedure was developed using Me3S(O)I, NaH, and Sc(OTf)3. The scope and limitations were briefly examined, and a tentative mechanism was proposed. Application of the methodology to known cyclobutanone 1 provided the corresponding cyclopentanone, which was successfully advanced to (+)-carbovir and (+)-aristeromycin.
