Diastereoselective synthesis of (±)-heliotropamide by a one-pot, four-component reaction.
The first synthesis of heliotropamide is reported. The preparation of this 2-oxopyrrolidine (γ-lactam) natural product relied on a diastereoselective one-pot, four-component reaction (4CR) for the assembly of the core structure. On the basis of chemical shift correlation and NOESY experiments, the previously unknown alkene geometry of heliotropamide is assigned as E.
Department of Chemistry, One Shields Ave, University of California, Davis, California 95616, USA.
Ashkaan
A
Younai
Gregory F
GF
Chin
Jared T
JT
Shaw
D007769:Lactams / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D007769:Lactams; D011759:Pyrrolidines; C482753:heliotropamide