Stereoselective Formal Synthesis of (+)-Allokainic Acid via Thiol-Mediated Acyl Radical Cyclization

被引：19

作者：

Yamada, Ken-ichi ^{[1
]}

Sato, Tomohiro ^{[1
]}

Hosoi, Masaki ^{[1
]}

Yamamoto, Yasutomo ^{[2
]}

Tomioka, Kiyoshi ^{[2
]}

机构：

[1] Kyoto Univ, Grad Sch Pharmaceut Sci, Sakyo Ku, Kyoto 606, Japan

[2] Doshisha Womens Coll Liberal Arts, Fac Pharmaceut Sci, Kyoto 6100395, Japan

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 2010年 / 58卷 / 11期

基金：

日本学术振兴会; 日本科学技术振兴机构;

关键词：

(+)-allokainic acid; acyl radical cyclization; thiol; stereoselective synthesis; C-H INSERTION; (+)-ALPHA-ALLOKAINIC ACID; ENANTIOSELECTIVE SYNTHESIS; (-)-ALPHA-KAINIC ACID; CARBOCYCLIZATION; CONSTRUCTION; PYRROLIDINES; KAINOIDS; BOND;

D O I：

10.1248/cpb.58.1511

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Stereoselective formal synthesis of (+)-allokainic acid was accomplished starting from L-glutamate by using a thiol-mediated acyl radical cyclization as a key step. The cyclization of a formylalkenoate proceeded in a highly diastereoselective manner to give trans-4,5-disubstituted pyrrolidin-3-one without the production of the cis-isomer. The pyrrolidinone was then converted into the established synthetic intermediate of (+)-allokainic acid via the iron-catalyzed coupling reaction with an isopropenyl Grignard reagent.

引用

页码：1511 / 1516

页数：6

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