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

The total synthesis of (−)-α-Kainic Acid 1 has been accomplished using ethyl N-Boc-pyroglutamate 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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Bibliographic Details
Published in:Tetrahedron letters 1998-04, Vol.39 (15), p.2171-2174
Main Authors: Rubio, Almudena, Ezquerra, Jesús, Escribano, Ana, Remuiñán, Modesto Jesús, Vaquero, Juan José
Format: Article
Language:English
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Summary:The total synthesis of (−)-α-Kainic Acid 1 has been accomplished using ethyl N-Boc-pyroglutamate 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. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(98)00166-X