title: Stereocontrolled synthesis of (-)-galanthamine.
abstract: An enantioselective synthesis of (-)-galanthamine has been realized in 11 linear steps starting from isovanillin. A Mitsunobu aryl ether forming reaction was used to assemble the galanthamine backbone, which was stitched together using enyne ring-closing metathesis, Heck, and N-alkylation reactions affording the tetracyclic ring system. Control of relative and absolute stereochemistry was derived from an easily accessible enantiomerically enriched propargylic alcohol 13.
authors: School of Chemistry, University of Southampton, Highfield, Southampton, UK.
authors: Vachiraporn
authors: V
authors: Satcharoen
authors: Neville J
authors: NJ
authors: McLean
authors: Stephen C
authors: SC
authors: Kemp
authors: Nicholas P
authors: NP
authors: Camp
authors: Richard C D
authors: RC
authors: Brown
mesh_terms: D003500:Cyclization; D005702:Galantamine / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D005702:Galantamine