Epoxide opening-induced tandem 8-azabicyclo[3.2.1]octane to 6-azabicyclo[3.2.1]octane rearrangement-iminium allylation: synthesis of (+/-)-peduncularine.
An efficient Lewis acid induced nitrogen-driven rearrangement iminium-trapping cascade from an epoxytropinone 3 gives a 7-allylated 6-azabicyclo[3.2.1]octan-3-one 2, which is converted into the alkaloid (+/-)-peduncularine (1).
Hodgson
David M
DM
Department of Chemistry, University of Oxford, Chemistry Research Laboratory, UK. david.hodgson@chem.ox.ac.uk
Shelton
Ruth E
RE
Moss
Thomas A
TA
Dekhane
Mouloud
M
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D053961:Azabicyclo Compounds / Q000737:chemistry*; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009795:Octanes / Q000737:chemistry*; D013237:Stereoisomerism
D000470:Alkaloids; D053961:Azabicyclo Compounds; D026121:Indole Alkaloids; D009795:Octanes; C467792:peduncularine