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

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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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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container_title Organic letters
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creator Hodgson, David M
Hachisu, Shuji
Andrews, Mark D
description 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.
doi_str_mv 10.1021/ol047557u
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subjects Alkenes - chemistry
Bridged Bicyclo Compounds, Heterocyclic - chemistry
Catalysis
Indicators and Reagents
Kainic Acid - analogs & derivatives
Kainic Acid - chemical synthesis
Molecular Structure
title Synthesis of α-Kainic Acid from a 7-Azabicyclo[2.2.1]heptadiene by Tandem Radical Addition−Homoallylic Radical Rearrangement
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