title: Synthesis of a D-ring isomer of galanthamine via a radical-based Smiles rearrangement reaction.
abstract: The 1,9-ethanoiminomethano-bridged tetrahydrodibenzo[b,d]-furan 2, a non-natural isomer of the alkaloid (-)-galanthamine (1) varying in the manner in which the D-ring is annulated to the ABC-core, has been prepared in racemic form. The synthetic sequence starts with the cyclopropane 3 and involves intramolecular Heck alkenylation and radical-based Smiles rearrangement reactions as key steps. Unlike natural product 1, but as predicted by docking studies, compound 2 is not a potent inhibitor of acetylcholine esterase.
authors: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 0200, Australia.
authors: Ping
authors: P
authors: Lan
authors: Colin J
authors: CJ
authors: Jackson
authors: Martin G
authors: MG
authors: Banwell
authors: Anthony C
authors: AC
authors: Willis
mesh_terms: D005609:Free Radicals / Q000737:chemistry; D005702:Galantamine / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005609:Free Radicals; D005702:Galantamine