title: Spirocyclic restriction of nucleosides. Synthesis of the first exemplary syn-1-oxaspiro[4.4]nonanyl member.
abstract: [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.
authors.affiliation: Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA. paquette.1@osu.edu
authors.forename: L A
authors.initials: LA
authors.lastname: Paquette
authors.forename: R T
authors.initials: RT
authors.lastname: Bibart
authors.forename: C K
authors.initials: CK
authors.lastname: Seekamp
authors.forename: A L
authors.initials: AL
authors.lastname: Kahane
mesh_terms: 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
chemical_list: D009705:Nucleosides; D010165:Palladium