Stereocontrolled Syntheses of Kainoid Amino Acids from 7-Azabicyclo[2.2.1]heptadienes Using Tandem Radical Addition-Homoallylic Radical Rearrangement

N-Boc syn-7-(2-hydroxyethyl)-4-(alkyl or aryl)sulfonyl-2-azabicyclo[2.2.1]hept-5-enes serve as precursors in syntheses of the neuroexcitants 3-(carboxymethyl)pyrrolidine-2,4-dicarboxylic acid 43, α-kainic acid 12, α-isokainic acid 14, and α-dihydroallokainic acid 77. The key step in these syntheses...

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Veröffentlicht in:	Journal of organic chemistry 2005-10, Vol.70 (22), p.8866-8876
Hauptverfasser:	Hodgson, David M, Hachisu, Shuji, Andrews, Mark D
Format:	Artikel
Sprache:	eng
Schlagworte:	Alcohols - chemistry Alkylation Amino Acids - chemical synthesis Amino Acids - chemistry Aza Compounds - chemical synthesis Aza Compounds - chemistry Chemistry Cyclization Exact sciences and technology Free Radicals - chemistry Heterocyclic compounds Heterocyclic compounds with only one n hetero atom and condensed derivatives Hydrogen - chemistry Iodine - chemistry Kainic Acid - chemistry Lactones - chemistry Molecular Structure Organic chemistry Oxidation-Reduction Preparations and properties Pyrrolidines - chemistry Stereoisomerism Sulfhydryl Compounds - chemistry Sulfur - chemistry Temperature
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