title: Synthesis and functionalization of bicyclic N,O-acetal scaffolds from furfural.
abstract: We have synthesized biologically relevant 6-aza-8-oxa[3.2.1]bicyclooctane scaffolds in a five-step procedure starting from furfural. Besides showing that these scaffolds are amenable to decoration via standard functional group interconversions, we also describe investigations for further functionalization via Lewis acid-mediated N,O-acetal opening, followed by nucleophilic trapping of the resulting intermediate cation. By using different nucleophiles, we have successfully prepared a modest library of 2,6-trans-disubstituted pyrans in good yields and in a highly diastereoselective manner.
authors.affiliation: Radboud University Nijmegen, Institute for Molecules and Materials, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
authors.forename: Ferdi
authors.initials: F
authors.lastname: van der Pijl
authors.affiliation: Radboud University Nijmegen, Institute for Molecules and Materials, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands.
authors.forename: Floris L
authors.initials: FL
authors.lastname: van Delft
authors.affiliation: Radboud University Nijmegen, Institute for Molecules and Materials, Heyendaalseweg 135, 6525 AJ Nijmegen, The Netherlands. Electronic address: F.Rutjes@science.ru.nl.
authors.forename: Floris P J T
authors.initials: FP
authors.lastname: Rutjes
mesh_terms: D000080:Acetals / Q000737:chemistry*; D001372:Aza Compounds / Q000737:chemistry*; D001391:Azo Compounds / Q000737:chemistry*; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D002384:Catalysis; D055808:Drug Discovery; D005662:Furaldehyde / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000080:Acetals; D001372:Aza Compounds; D001391:Azo Compounds; D001643:Bridged Bicyclo Compounds; D005662:Furaldehyde
keywords: Furfural; Heterocyclic scaffold; N,O-Acetal; N-Acyliminium ion; Substituted pyrans