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

Ashkaan Younai; Gregory F Chin; Jared T Shaw

doi:10.1021/jo1019317

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

J Org Chem. 2010 Dec 3;75(23):8333-6. doi: 10.1021/jo1019317. Epub 2010 Nov 9.

Authors

Ashkaan Younai¹, Gregory F Chin, Jared T Shaw

Affiliation

¹ Department of Chemistry, One Shields Ave, University of California, Davis, California 95616, USA.

PMID: 21062051
DOI: 10.1021/jo1019317

Abstract

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.

Publication types

Research Support, Non-U.S. Gov't
Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

Lactams / chemical synthesis*
Lactams / chemistry
Magnetic Resonance Spectroscopy
Molecular Structure
Pyrrolidines / chemical synthesis*
Pyrrolidines / chemistry
Stereoisomerism

Substances

Lactams
Pyrrolidines
heliotropamide