Stereoselective synthesis of (+)-euphococcinine and (-)-adaline.
We describe the syntheses of (+)-euphococcinine and (-)-adaline, two naturally occurring alkaloids containing a quaternary carbon bearing a nitrogen atom. Key features of the syntheses are a 3,3-sigmatropic rearrangement to give an all-carbon quaternary center, a ring-closing alkene metathesis to give an 8-membered ring, and the use of a single enantiomer of p-menthane-3-carboxaldehyde to make two natural alkaloids of opposite configuration.
Arbour
Mélissa
M
Université de Sherbrooke, Département de Chimie, Sherbrooke, Quebec, Canada J1K 2R1.
Roy
Stéphanie
S
Godbout
Cédrickx
C
Spino
Claude
C
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D001952:Bridged-Ring Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D002244:Carbon / Q000737:chemistry; D003485:Cyanates / Q000737:chemistry; D003500:Cyclization; D017953:Isocyanates / Q000737:chemistry; D009584:Nitrogen / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D013379:Substrate Specificity
D000470:Alkaloids; D001952:Bridged-Ring Compounds; D003485:Cyanates; D017953:Isocyanates; D010880:Piperidines; C475960:adaline; C048057:euphococcinine; D002244:Carbon; D009584:Nitrogen