Diastereoselective synthesis of fused lactone-pyrrolidinones; application to a formal synthesis of (-)-salinosporamide A

Angus W J Logan; Simon J Sprague; Robert W Foster; Léo B Marx; Vincenzo Garzya; Michal S Hallside; Amber L Thompson; Jonathan W Burton

doi:10.1021/ol501662t

Diastereoselective synthesis of fused lactone-pyrrolidinones; application to a formal synthesis of (-)-salinosporamide A

Org Lett. 2014 Aug 15;16(16):4078-81. doi: 10.1021/ol501662t. Epub 2014 Jul 28.

Authors

Angus W J Logan¹, Simon J Sprague, Robert W Foster, Léo B Marx, Vincenzo Garzya, Michal S Hallside, Amber L Thompson, Jonathan W Burton

Affiliation

¹ Chemistry Research Laboratory, Department of Chemistry, University of Oxford , Mansfield Road, Oxford OX1 3TA, United Kingdom.

PMID: 25068416
DOI: 10.1021/ol501662t

Abstract

A mild, diastereoselective synthesis of fused lactone-pyrrolidinones using an oxidative radical cyclization is reported. The methodology is demonstrated in a formal synthesis of (-)-salinosporamide A.

Publication types

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

MeSH terms

Cyclization
Lactones / chemical synthesis*
Lactones / chemistry
Molecular Structure
Oxidation-Reduction
Pyrroles / chemical synthesis*
Pyrroles / chemistry
Pyrrolidinones / chemical synthesis*
Pyrrolidinones / chemistry
Stereoisomerism

Substances

Lactones
Pyrroles
Pyrrolidinones
marizomib