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ChemInform Abstract: Stereoselective Synthesis of (.+-.)-α-Kainic Acid Using Free Radical Key Reactions.

✍ Scribed by M. D. BACHI; N. BAR-NER; A. MELMAN


Publisher
John Wiley and Sons
Year
2010
Weight
38 KB
Volume
28
Category
Article
ISSN
0931-7597

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✦ Synopsis


Stereoselective Synthesis of (±)-α-Kainic Acid Using Free Radical Key Reactions. -The title compound (XI) is obtained via two routes from the highly substituted isocyanide and the isothiocyanate (XII) via the common intermediate (IX). In both routes the key synthons (cf. (IV) and (XIV)) are obtained by a free radical cyclization. -(BACHI, M. D.; BAR-NER, N.;


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A Formal Synthesis of (-)-α-Kainic Acid. -Starting from Lpyroglutamic acid (-)-(I), the known precursor (-)-(XVI) for the synthesis of the title compound is presented. The key step in this approach is the SmI 2 -mediated ketyl radical cyclization of the enecarbamate (X). Under irradiation condition