title: Synthesis of novel spiro[2.3]hexane carbocyclic nucleosides via enzymatic resolution.
abstract: [reaction: see text] Novel R- and S-spiro[2.3]hexane nucleosides have been synthesized. The key step involved the Pseudomonas cepacia lipase catalyzed resolution of racemic compound 2, synthesized in seven steps starting from diethoxyketene and diethyl fumarate, to give (+)-acetate 3 and (-)-alcohol 13. (+)-Acetate 3 and (-)-acetate 14 were converted to R- and S-9-(6-hydroxymethylspiro[2.3]hexane)-4-adenine, respectively.
authors.affiliation: Department of Pharmaceutical and Biomedical Sciences, College of Pharmacy, The University of Georgia, Athens, Georgia 30602, USA.
authors.forename: Lavanya
authors.initials: L
authors.lastname: Bondada
authors.forename: Giuseppe
authors.initials: G
authors.lastname: Gumina
authors.forename: Ranjeet
authors.initials: R
authors.lastname: Nair
authors.forename: Xing Hai
authors.initials: XH
authors.lastname: Ning
authors.forename: Raymond F
authors.initials: RF
authors.lastname: Schinazi
authors.forename: Chung K
authors.initials: CK
authors.lastname: Chu
mesh_terms: D000085:Acetates / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry; D016956:Burkholderia cepacia / Q000201:enzymology*; D002384:Catalysis; D005650:Fumarates / Q000737:chemistry; D006586:Hexanes / Q000737:chemistry*; D008049:Lipase / Q000378:metabolism*; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D009705:Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D000085:Acetates; D000438:Alcohols; D005650:Fumarates; D006586:Hexanes; D009705:Nucleosides; C026385:n-hexane; C035088:diethyl fumarate; D008049:Lipase