Enantioselective access to isoquinuclidines by tropenone desymmetrization and homoallylic radical rearrangement: synthesis of (+)-ibogamine.
[reaction: see text]. Chiral lithium amide-induced desymmetrization of a tropenone and subsequent Bu3SnH-catalyzed nitrogen-directed homoallylic radical rearrangement constitute key steps in a new strategy to dehydroisoquinuclidines. The strategy was applied in a synthesis of (+)-ibogamine.
Hodgson
David M
DM
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. david.hodgson@chem.ox.ac.uk
Galano
Jean-Marie
JM
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D015394:Molecular Structure; D011812:Quinuclidines / Q000737:chemistry*; D013237:Stereoisomerism; D030014:Tabernaemontana / Q000737:chemistry
D000470:Alkaloids; D001952:Bridged-Ring Compounds; D011812:Quinuclidines; C413805:ibogamine