Diastereoselective synthesis of (±)-heliotropamide by a one-pot, four-component reaction.

J Org Chem

Department of Chemistry, One Shields Ave, University of California, Davis, California 95616, USA.

Published: December 2010

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.

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http://dx.doi.org/10.1021/jo1019317DOI Listing

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