title: A remarkably simple chemicoenzymatic approach to structurally complex bicyclo[3.1.0]hexane carbocyclic nucleosides.
abstract: [reaction: see text] Intramolecular cyclopropanation of a carbene engendered from the corresponding diazo beta-ketoester produced the desired bicyclo[3.1. 0]hexane pseudosugar. Purine nucleosides obtained via Mitsunobu coupling were resolved with adenosine deaminase. The requisite beta-ketoester was assembled in one step from ethyl acetoacetate and acrolein.
authors: Laboratory of Medicinal Chemistry, Division of Basic Sciences, National Cancer Institute, FCRDC, Frederick, Maryland 21702-1201, USA.
authors: H R
authors: HR
authors: Moon
authors: H
authors: H
authors: Ford
authors: V E
authors: VE
authors: Marquez
mesh_terms: D000090:Acetoacetates; D000171:Acrolein; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis*; D002851:Chromatography, High Pressure Liquid; D003500:Cyclization; D007202:Indicators and Reagents; D009705:Nucleosides / Q000138:chemical synthesis*; D011487:Protein Conformation
chemical_list: D000090:Acetoacetates; D001643:Bridged Bicyclo Compounds; D007202:Indicators and Reagents; D009705:Nucleosides; D000171:Acrolein