Spirocyclic restriction of nucleosides. Synthesis of the first exemplary syn-1-oxaspiro[4.4]nonanyl member.
[reaction: see text] The potential benefits associated with the spirocyclic restriction of nucleosides are summarized. Following exploration of a pi-allylpalladium route to 5'-alpha- or syn-dideoxy examples, we evaluated MOM protection of the 5'-hydroxyl as being suited to the synthesis of the first member of this new class of nucleoside mimic.
Paquette
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LA
Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA. paquette.1@osu.edu
Bibart
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RT
Seekamp
C K
CK
Kahane
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AL
D018360:Crystallography, X-Ray; D003500:Cyclization; D008968:Molecular Conformation; D018716:Molecular Mimicry; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis / Q000737:chemistry*; D010165:Palladium / Q000737:chemistry
D009705:Nucleosides; D010165:Palladium