Synthesis of alpha-kainic acid from a 7-azabicyclo[2.2.1]heptadiene by tandem radical addition-homoallylic radical rearrangement

David M Hodgson; Shuji Hachisu; Mark D Andrews

doi:10.1021/ol047557u

Synthesis of alpha-kainic acid from a 7-azabicyclo[2.2.1]heptadiene by tandem radical addition-homoallylic radical rearrangement

Org Lett. 2005 Mar 3;7(5):815-7. doi: 10.1021/ol047557u.

Authors

David M Hodgson¹, Shuji Hachisu, Mark D Andrews

Affiliation

¹ Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford OX1 3TA, UK. david.hodgson@chem.ox.ac.uk

PMID: 15727448
DOI: 10.1021/ol047557u

Abstract

Reductive radical addition of 2-iodoethanol to N-Boc 2-tosyl-7-azabicyclo[2.2.1]heptadiene gives N-Boc syn-7-(2-hydroxyethyl)-4-tosyl-2-azabicyclo[2.2.1]hept-5-ene, which is converted into the neuroexcitants 3-(carboxymethyl)pyrrolidine-2,4-dicarboxylic acid and alpha-kainic acid. [structure: see text]

Publication types

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

MeSH terms

Alkenes / chemistry*
Bridged Bicyclo Compounds, Heterocyclic / chemistry*
Catalysis
Indicators and Reagents
Kainic Acid / analogs & derivatives*
Kainic Acid / chemical synthesis*
Molecular Structure

Substances

Alkenes
Bridged Bicyclo Compounds, Heterocyclic
Indicators and Reagents
Kainic Acid