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Approaches to a synthesis of α-kainic acid

✍ Scribed by Janine Cossy; Manuel Cases; Domingo Gomez Pardo

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
920 KB
Volume
55
Category
Article
ISSN
0040-4020

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✦ Synopsis

A formal synthesis of (-)-a-kainic acid was achieved from L-pyroglutamic acid. The C-4 substituent of the pyrrolidine ring was introduced by using a ketyl radical cyclization on an ene carbamate.

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The total synthesis of (-)-ot-Kainic Acid 1 has been accomplished using ethyl N-Bocpyroglutamate 2 as starting material. The isopropenyl appendage was achieved from the elimination of the dimethylcarbinol introduced at C-4 via an aldol condensation of the lactam enolate of 2 and acetone. The acetate

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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

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