New enantioselective approach to the total synthesis of (-)-α-kainic acid

被引：39
|
作者：
Rubio, A
Ezquerra, J
Escribano, A
Remuiñán, MJ
Vaquero, JJ
机构：
[1] Ctr Invest Lilly, Madrid 28108, Spain
[2] Univ Alcala de Henares, Dept Quim Organ, Madrid 28871, Spain
来源：
TETRAHEDRON LETTERS | 1998年 / 39卷 / 15期
关键词：
D O I：
10.1016/S0040-4039(98)00166-X
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The total synthesis of (-)-alpha-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. (C) 1998 Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：2171 / 2174
页数：4
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