Nitrogen heterocycles via palladium-catalyzed carbocyclization. Formal synthesis of (+)-alpha-allokainic acid

Gregory R Cook; Liangdong Sun

doi:10.1021/ol049087+

Nitrogen heterocycles via palladium-catalyzed carbocyclization. Formal synthesis of (+)-alpha-allokainic acid

Org Lett. 2004 Jul 8;6(14):2481-4. doi: 10.1021/ol049087+.

Authors

Gregory R Cook¹, Liangdong Sun

Affiliation

¹ Center for Protease Research, Department of Chemistry and Molecular Biology, North Dakota State University, P.O. Box 5516, Fargo, North Dakota 58105-5516, USA. gregory.cook@ndsu.nodak.edu

PMID: 15228309
DOI: 10.1021/ol049087+

Abstract

[reaction: see text] The Pd-catalyzed carbocyclization of ketoamides was investigated and found to be highly dependent on the phosphine ligand as well as the presence of coordinating counterions. Nitrogen heterocycles were formed without erosion of the stereochemical integrity. The utility of the lactam products was demonstrated by the formal synthesis of (+)-alpha-allokainic acid.

Publication types

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

MeSH terms

Catalysis
Cyclization
Indicators and Reagents
Kainic Acid / analogs & derivatives*
Kainic Acid / chemical synthesis*
Molecular Structure
Nitrogen / chemistry*
Palladium / chemistry*
Phosphines / chemistry
Stereoisomerism

Substances

Indicators and Reagents
Phosphines
allokainic acid
Palladium
Nitrogen
Kainic Acid

Grants and funding

P20-RR15566/RR/NCRR NIH HHS/United States