title: Syntheses of new spirocarbocyclic nucleoside analogs using iminonitroso Diels-Alder reactions.
abstract: N-Cbz- and Boc-protected spirocyclic dienes were prepared by dialkylation of cyclopentadiene. These dienes coupled efficiently in a series of iminonitroso Diels-Alder reactions to produce a series of new spirocyclic adducts. Hydrogenolysis of these adducts afforded new spirocycles that contain multiple handles for further functionalization. Furthermore, stereocontrolled dihydroxylation and reductive cleavage of the spirocyclic adducts generated versatile scaffolds for the syntheses and derivatization of novel spirocyclic carbocyclic nucleoside analogs.
authors.affiliation: Department of Chemistry and Biochemistry, University of Notre Dame, Notre Dame, Indiana 46556, USA.
authors.forename: Weimin
authors.initials: W
authors.lastname: Lin
authors.forename: Anuradha
authors.initials: A
authors.lastname: Gupta
authors.forename: Kyung Hee
authors.initials: KH
authors.lastname: Kim
authors.forename: David
authors.initials: D
authors.lastname: Mendel
authors.forename: Marvin J
authors.initials: MJ
authors.lastname: Miller
mesh_terms: D006865:Hydrogenation; D007097:Imines / Q000737:chemistry*; D009603:Nitroso Compounds / Q000737:chemistry*; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013141:Spiro Compounds / Q000737:chemistry*
chemical_list: D007097:Imines; D009603:Nitroso Compounds; D009705:Nucleosides; D013141:Spiro Compounds