Synthesis of α-Kainic Acid from a 7-Azabicyclo[2.2.1]heptadiene by Tandem Radical Addition−Homoallylic Radical Rearrangement

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 α-kainic acid.

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Bibliographische Detailangaben
Veröffentlicht in:	Organic letters 2005-03, Vol.7 (5), p.815-817
Hauptverfasser:	Hodgson, David M, Hachisu, Shuji, Andrews, Mark D
Format:	Artikel
Sprache:	eng
Schlagworte:	Alkenes - chemistry Bridged Bicyclo Compounds, Heterocyclic - chemistry Catalysis Indicators and Reagents Kainic Acid - analogs & derivatives Kainic Acid - chemical synthesis Molecular Structure
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Beschreibung
Zusammenfassung:	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 α-kainic acid.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/ol047557u