Improved and Practical Synthesis of the Integrastatin Core

• Yoshiro Yamagiwa

  Department of Chemistry, Faculty of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502 , Japan

• Nozomi Haruna

  Department of Chemistry, Faculty of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502 , Japan

• Hideki Kawakami

  Department of Chemistry, Faculty of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502 , Japan

• Kouichi Matsumoto

  Department of Chemistry, Faculty of Science and Engineering, Kindai University, 3-4-1 Kowakae, Higashi-Osaka, Osaka 577-8502 , Japan

Abstract

The new and versatile method for the synthesis of integrastatin core has been developed by the use of o-toluic acid and 2′-hydroxyacetophenone with NaH/sec-BuLi, followed by the reaction of dihydroisocoumarins with MeLi. The overall steps for the synthesis of integrastatin core was only 3 steps including the known method by the literature. The scope and limitations of substrates bearing the various substituents on the aromatic ring were investigated. The chemical yields by our approach are generally high and the current route enables us the rapid synthesis.

Journal

• Bulletin of the Chemical Society of Japan

  Bulletin of the Chemical Society of Japan 93 (8), 1036-1042, 2020-05-15

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360285711965075584
• NII Article ID: 130007887996
• DOI: 10.1246/bcsj.20200070
• ISSN: 13480634
• ISSN: 00092673
• Web Site: https://academic.oup.com/bcsj/article-pdf/93/8/1036/56304932/bcsj.20200070.pdf
• Data Source:
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  • CiNii Articles
  • KAKEN