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New enantioselective approach to the total synthesis of (−)-α-Kainic Acid

✍ Scribed by Almudena Rubio; Jesús Ezquerra; Ana Escribano; Modesto Jesús Remuiñán; Juan José Vaquero

Publisher
Elsevier Science
Year
1998
Tongue
French
Weight
269 KB
Volume
39
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 group at C-3 of the kainic acid structure was introduced via diethyl malonate Michael addition reaction to the 2,3-didehydroprolinate 8. This Michael addition reaction proceeds with complete stereocontrol over the newly generated stereogenic centres. Inversion of the configuration at C-3 in 9 through double bond formation followed by hydrogenation, neutral decarboxylation and further epimerization of the C-2 stereogenic centre in 12, gave rise to the desired natural product.

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