Stereocontrolled synthesis of (-)-galanthamine.
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.
Satcharoen
Vachiraporn
V
School of Chemistry, University of Southampton, Highfield, Southampton, UK.
McLean
Neville J
NJ
Kemp
Stephen C
SC
Camp
Nicholas P
NP
Brown
Richard C D
RC
D003500:Cyclization; D005702:Galantamine / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D005702:Galantamine