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

• Yamada Ken-ichi

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Sato Tomohiro

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Hosoi Masaki

  Graduate School of Pharmaceutical Sciences, Kyoto University

• Yamamoto Yasutomo

  Faculty of Pharmaceutical Sciences, Doshisha Women's College of Liberal Arts

• Tomioka Kiyoshi

  Faculty of Pharmaceutical Sciences, Doshisha Women's College of Liberal Arts

Bibliographic Information

Other Title

• Stereoselective formal synthesis of (+)-allokainic acid via thiol-mediated acyl radical cyclization

Abstract

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.

Journal

• Chemical and Pharmaceutical Bulletin

  Chemical and Pharmaceutical Bulletin 58 (11), 1511-1516, 2010

  The Pharmaceutical Society of Japan

Keywords

• (+)-allokainic acid
• acyl radical cyclization
• thiol
• stereoselective synthesis

Details

• CRID: 1390001204172484480
• NII Article ID: 130000405667
• NII Book ID: AA00602100
• DOI: 10.1248/cpb.58.1511
• ISSN: 13475223
• ISSN: 00092363
• NDL BIB ID: 10859334
• Web Site: https://ndlsearch.ndl.go.jp/books/R000000004-I10859334
• Web Site: https://www.jstage.jst.go.jp/article/cpb/58/11/58_11_1511/_pdf
• Text Lang: en
• Data Source:
  • JaLC
  • NDL
  • Crossref
  • CiNii Articles
  • KAKEN
• Abstract License Flag: Disallowed