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Stereocontrolled syntheses of kainoid amino acids from 7-azabicyclo[2.2.1]heptadienes using tandem radical addition-homoallylic radical rearrangement.

Abstract:

[reaction; see text] 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, alpha-kainic acid 12, alpha-isokainic acid 14, and alpha-dihydroallokainic acid 77. The key step in these syntheses is the intermolecular radical addition of 2-iodoethanol to a N-Boc 2-(alkyl or aryl)sulfonyl-7-azabicyclo[2.2.1]heptadiene 7 to induce nitrogen-directed homoallylic...

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Publication status:
Published

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Publisher copy:
10.1021/jo0513865

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Institution:
University of Oxford
Department:
Oxford, MPLS, Chemistry, Organic Chemistry
Role:
Author
Journal:
The Journal of organic chemistry
Volume:
70
Issue:
22
Pages:
8866-8876
Publication date:
2005-10-05
DOI:
EISSN:
1520-6904
ISSN:
0022-3263
URN:
uuid:737b33dc-9f29-4508-9563-fb24cfc215fb
Source identifiers:
33275
Local pid:
pubs:33275

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