A remarkably simple chemicoenzymatic approach to structurally complex bicyclo[3.1.0]hexane carbocyclic nucleosides.
[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.
Moon
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Laboratory of Medicinal Chemistry, Division of Basic Sciences, National Cancer Institute, FCRDC, Frederick, Maryland 21702-1201, USA.
Ford
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Marquez
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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
D000090:Acetoacetates; D001643:Bridged Bicyclo Compounds; D007202:Indicators and Reagents; D009705:Nucleosides; D000171:Acrolein